WO2017109722A1 - Composés hétérocycliques azotés et dispositifs électroluminescents organiques contenant ceux-ci - Google Patents

Composés hétérocycliques azotés et dispositifs électroluminescents organiques contenant ceux-ci Download PDF

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WO2017109722A1
WO2017109722A1 PCT/IB2016/057876 IB2016057876W WO2017109722A1 WO 2017109722 A1 WO2017109722 A1 WO 2017109722A1 IB 2016057876 W IB2016057876 W IB 2016057876W WO 2017109722 A1 WO2017109722 A1 WO 2017109722A1
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substituted
unsubstituted
carbon atoms
ring
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Yuichi Nishimae
Yuki Nakano
Hideaki Nagashima
Natalia Chebotareva
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Idemitsu Kosan Co., Ltd.
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Priority to US16/064,296 priority Critical patent/US20190006601A1/en
Publication of WO2017109722A1 publication Critical patent/WO2017109722A1/fr

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Definitions

  • the present invention relates to compounds of general formulae (I) and (1 1 ), to an electronic device comprising at least one of these compounds, to an emitting layer, preferably present in an electronic device, comprising at least one compound of general formula (I) or (1 1 ) and to the use of a compound according to general formula (I) or (1 1 ) in an electronic device as a host material, a charge transporting material, a charge and/or exciton blocking material, preferably as a host material or an electron transporting material.
  • X may be O or H2 and Ri , R2, R3 and R 4 may be hydro- gen, Ri and R2 may form a six membered ring or R3 and R 4 may be an additional bond, and a process for their preparation.
  • This document further discloses that the mentioned compounds show activities in a number of pharmaceutical applications based on their sedative, CNS- depressant, neuroleptic, hypnotic, analgesic, diuretic, anthelminthic, antimicrobial, antitubercu- lar, antibiotic antihypertensive, antiinflammatory and antitumoral properties.
  • each of Ri to F3 ⁇ 4, R 7 to R16, R18 to R20, R22 to R25 may be alkyl, aryl, or heteroaryl, and may be direct bond or arylene. Only the compounds having the following structure:
  • Ri to R 4 and R 7 to R16 are all hydrogen, are actually described as exemplified compounds. This document further discloses their use as electroluminescent device materials.
  • the present invention provides materials suitable for use in electronic devices, preferably OLEDs, and further applications in organic electronics. More particularly, it should be possible to provide electronic devices comprising new compounds as electron transport materials, as hole transport materials or as host materials.
  • the materials should be suitable especially for OLEDs which comprise at least one emitter, which is preferably a phosphorescence emitter, for example at least one red phosphorescent emitter, especially as a host material.
  • the materials should also be suitable especially for OLEDs which comprise at least one emitter, which is preferably a fluorescence emitter, for example at least one blue fluorescent emitter, especially as an electron transporting material.
  • the materials should be suitable for providing electronic devices, preferably OLEDs, which ensure good efficiencies and a low use and operating voltage of the OLEDs.
  • X 10 isCR 10 orN, wherein X 1 and X 3 are not CR 1 and CR 3 at the same time,
  • Y is selected from NR 11 , O or S,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are independently of each other selected from H, E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C2salkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, or at least two of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 , if present at adjacent carbon atoms, together form at least one C6-Cisaryl or Ci-Cish
  • L 1 , L 2 , L 3 and L 4 are independently of each other selected from a C6-C4oaryl group which is unsubstituted or substituted by at least one group E, Ci-C24heteroaryl group which is unsubstituted or substituted by at least one group E, R 14 is independently of each other selected from H , E, a C6-C2 4 aryl group which is unsubstituted or substituted by at least one group E, Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E, a Ci-C2salkyl group which unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E,
  • E is independently of each other -OR 21 , -SR 21 , -N R 17 R 18 , -COR 20 , -COOR 19 , -CON R 17 R 18 , -CN , - SiR 22 R 23 R 24 , halogen, a C6-C6oaryl group which is unsubstituted or is substituted by at least one -F, -CF 3 , -CF2CF3, -CF2CF2CF3, -CF(CF 3 )2, -(CF2)3CF 3 or -C(CF 3 ) 3 , a Ci-Ci 8 alkyl or a Ci-Ci 8 alkyl group which is interrupted by at least one O, a Ci-C6oheteroaryl group which is unsubstituted or substituted by at least one -F, -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -(
  • R 15 and R 16 are independently of each other H , a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group which is interrupted by at least one O,
  • R 17 and R 18 are independently of each other H , a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O, or R 17 and R 18 together form a five or six membered aliphatic, aromatic or heteroaromatic ring,
  • R 19 is H , a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O,
  • R 20 is H or a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cis alkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O
  • R 21 is independently of each other H , a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci- Cisalkyl group, which is interrupted by at least one O,
  • R 22 ' R 23 and R 24 are independently of each other H , a Ci-Cisalkyl group, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group, and R 25 is H, a Ci-Cisalkyl group, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E. [0013]
  • L 100 is selected from a direct bond, an arylene group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by at least one group G, or a heteroarylene group having 5 to 30 ring atoms which is unsubstituted or substituted by at least one group G;
  • n 100 is an integer selected from 1 to 4;
  • R 100 is selected from a hydrogen atom, an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted by at least one group G, a heterocyclic group having 3 to 30 ring atoms which is unsubstituted or substituted by at least one group G, or an alkyl group having 1 to 25 carbon atoms which is unsubstituted or substituted by at least one group G;
  • R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , R 108 , R 109 , R 110 , R 111 , R 112 , R 113 , R 114 , R 115 , and R 116 are independently of each other and selected from a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 25 carbon atoms which is unsubstituted or substi- tuted by at least one group G, an alkenyl group having 2 to 25 carbon atoms which is unsubstituted or substituted by at least one group G, an alkynyl group having 2 to 25 carbon atoms which is unsubstituted or substituted by at least one group G, a cycloalkyl group having 3 to 25 carbon atoms which is unsubstituted or substituted by at least one group G, an alkoxy group having 1 to 25 carbon atoms
  • G is independently of each other and selected from a halogen atom, a cyano group, an alkyl group having 1 to 25 carbon atoms, an alkenyl group having 2 to 25 carbon atoms, an alkynyl group having 2 to 25 carbon atoms, a cycloalkyl group having 3 to 25 carbon atoms, an alkoxy group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heterocyclic group having 3 to 30 ring atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylthio group having 1 to 25 carbon atoms, an arylthio group having 6 to 30 ring carbon atoms, a mono-, di-, or tri-substituted silyl group, wherein the substituent is selected from an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, a mono- or di-substitute
  • halogen, alkyl, aryl, aryloxy and heteroaryl general- ly have the following meaning, if said groups are not further specified in specific embodiments mentioned below.
  • Halogen is fluorine, chlorine, bromine and iodine.
  • Ci-C25alkyl preferably Ci-Cisalkyl, is typically linear or branched, where possible. Examples are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3- pentyl, 2,2-dimethylpropyl, 1 ,1 ,3,3-tetramethylpentyl, n-hexyl, 1-methylhexyl, 1 ,1 ,3,3,5,5- hexamethylhexyl, n-heptyl, isoheptyl, 1 ,1 ,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 1 ,1 ,3,3-tetramethylbutyl and 2-ethylhexyl, n-nonyl
  • Ci-Csalkyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2- dimethyl-propyl, n-hexyl, n-heptyl, n-octyl, 1 ,1 ,3,3-tetramethylbutyl and 2-ethylhexyl.
  • Ci-C4alkyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert.-butyl.
  • Ci-C25alkoxy groups are straight-chain or branched alkoxy groups, e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, am- yloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, un- decyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy and octade- cyloxy.
  • alkoxy groups e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, am- yloxy, isoamyloxy or tert
  • Ci-Csalkoxy examples are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec- butoxy, isobutoxy, tert.-butoxy, n-pentyloxy, 2-pentyloxy, 3-pentyloxy, 2,2-dimethylpropoxy, n- hexyloxy, n-heptyloxy, n-octyloxy, 1 ,1 ,3,3-tetramethylbutoxy and 2-ethylhexyloxy, preferably Ci- C 4 alkoxy such as typically methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert.-butoxy.
  • C6-C6oaryl preferably C6-C2 4 aryl, particularly preferably C6-Cisaryl, which optionally can be substituted, is typically phenyl, 4-methylphenyl, 4-methoxyphenyl, naphthyl, especially 1-naphthyl, or 2-naphthyl, biphenylyl, terphenylyl, pyrenyl, 2- or 9-fluorenyl, phenanthryl, or anthryl, which may be unsubstituted or substituted.
  • Phenyl, 1-naphthyl and 2-naphthyl are examples of a C6- Cioaryl group.
  • C6-C2 4 aryloxy which optionally can be substituted, is typically C6-Cioaryloxy, which optionally can be substituted by one, or more Ci-Csalkyl and/or Ci-Csalkoxy groups, such as, for example, phenoxy, 1-naphthoxy, or 2-naphthoxy.
  • Ci-C6oheteroaryl preferably C2-C3oheteroaryl, particularly preferably C2-Ci3heteroaryl, represents a ring with five to seven ring atoms or a condensed ring system, wherein nitrogen, oxygen or sulfur are the possible hetero atoms, and is typically a heterocyclic group with 5 to 40 atoms having at least six conjugated ⁇ -electrons such as thienyl, benzothiophenyl, dibenzothiophenyl, thianthrenyl, furyl, furfuryl, 2H-pyranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, phenoxy- thienyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, bipyridyl, triazinyl, pyrimidinyl, pyrazinyl, pyridazi- nyl, indolizinyl, is
  • Benzimidazo[1 ,2-a]benzimidazo-5-yl, ben- zimidazo[1 ,2-a]benzimidazo-2-yl, carbazolyl and dibenzofuranyl are examples of a C2- C heteroaryl group.
  • C 7 -C25aralkyl is for example benzyl, 2-benzyl-2-propyl, ⁇ -phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, co-phenyl-butyl, ⁇ , ⁇ -dimethyl-co-phenyl-butyl, ⁇ -phenyl-dodecyl, ⁇ -phenyl-octadecyl, o-phenyl- eicosyl or ⁇ -phenyl-docosyl, preferably C 7 -Cisaralkyl such as benzyl, 2-benzyl-2-propyl, ⁇ - phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, ⁇ , ⁇ -dimethyl-co-phenyl-butyl, o-phenyl- dodecyl or ⁇ -phenyl-octadecyl, and particularly preferred C 7
  • C5-Ci2cycloalkyl is for example cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cy- clodecyl, cycloundecyl, cyclododecyl, preferably cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, which may be unsubstituted or substituted.
  • Ci-Csalkyl a hydroxyl group, a mercapto group, Ci-Csalkoxy, Ci-Csalkylthio, halogen, halo-Ci-Csalkyl, or a cyano group.
  • the present invention relates to a compound of general formula (I):
  • X 1 , X 2 , ⁇ 3 ⁇ ⁇ 4 , ⁇ 5 ⁇ ⁇ 6 , ⁇ 7 , X 8 , X 9 , X 10 and Y have the meanings as mentioned above.
  • X 1 is CR 1 or N and X 3 is CR 3 or N, wherein the meanings of R 1 and R 3 are explained above.
  • X 1 and X 3 are not CR 1 and CR 3 at the same time, meaning that at least one of X 1 and X 3 is N, whereas the other one is CR 1 or CR 3 , or both of X 1 and X 3 are N .
  • the present invention relates to the compound according to the present invention, wherein X 1 and X 3 are N.
  • Compounds of this preferred type correspond to the following formula (II):
  • the present invention relates to the compound according to the present invention, wherein X 1 is CR 1 and X 3 is N or X 1 is N and X 3 is CR 3 , wherein R 1 and R 3 have independently of each other the meanings as mentioned above.
  • Compounds of these preferred types correspond to the following formulae (III) and (IV):
  • the present invention relates to the compound according to the present invention, wherein X 1 is N and X 3 is CR 3 , wherein R 3 has the meanings as mentioned above.
  • Y may be selected from NR 11 , O or S, wherein R 11 has the meanings as mentioned above.
  • the present invention preferably relates to compounds according to the following general formulae (I la), (lib) and (lie):
  • the present invention relates to compounds according to the following general formulae (Ilia), (1Mb) and (lllc):
  • the present invention relates to compounds according to the following general formulae (IVa), (IVb) and (IVc)
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are independently of each other selected from H, E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C2salkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5- Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, or at least two of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 , if present at adjacent carbon atoms, together form at least one C6-Cis
  • R 15 and R 16 are independently of each other H, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group which is interrupted by at least one O, preferably H,
  • R 17 and R 18 are independently of each other H, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O, preferably H, C1-C18 alkyl group,
  • R 17 and R 18 together form a five or six membered aliphatic, aromatic or heteroaromatic ring, preferably five or six membered aliphatic ring
  • R 19 is H, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O, preferably H, a C6-Cisaryl group which is unsubstituted or a Ci- Cisalkyl group
  • R 20 is H or a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a C1-C18 alkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O, preferably H, a C6-
  • R 25 and R 27 are independently of each other H , a Ci-Cisalkyl group, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group, a C 7 -C25aralkyl which is unsubsti- tuted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, preferably H, a C6-Cisaryl group which is unsubstituted or a Ci-Cisalkyl group.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are independently of each other selected from a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 ) q -(L 4 )r R 14 , a Ci-C25alkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, wherein o is independently of each other 0 or 1 , p is independently of each other 0 or 1 , q is independently of each other 0 or 1 and r is independently of each other 0 or 1 , and L 1 , L 2 , L 3 and L 4 are independently of each other selected from a C6- C 40 aryl group which is unsubstituted or substituted by at least one group E, Ci-C2 4 heteroaryl
  • R 14 o is independently of each other 1
  • p is inde- pendently of each other 1
  • q is independently of each other 1
  • r is independently of each other 1.
  • L 1 is present, followed by L 2 , followed by L 3 , followed by L 4 , followed by R 14 .
  • o is independently of each other 1
  • p is inde- pendently of each other 1
  • q is independently of each other 1
  • r is independently of each other 0.
  • o is independently of each other 1
  • p is inde- pendently of each other 1
  • q is independently of each other 0
  • r is independently of each other 0.
  • o is independently of each other 1
  • p is inde- pendently of each other
  • q is independently of each other 0
  • r is independently of each other 0.
  • L 1 is present, followed by R 14 , wherein L 4 , L 3 and L 2 are not present.
  • o is independently of each other
  • p is inde- pendently of each other
  • q is independently of each other 0
  • r is independently of each other 0.
  • This preferred embodiment means that the compounds are substituted by R 14 , wherein L 4 , L 3 , L 2 and L 1 are not present.
  • L 1 , L 2 , L 3 and L 4 are independently of each other, if present, selected from a C6- C 40 aryl group which is unsubstituted or substituted by at least one group E or from a Ci- C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E.
  • L 1 . L 2 , L 3 and L 4 are independently of each other, if present, selected from a C6-C 4 oaryl group which is unsubstituted or from a Ci-C2 4 heteroaryl group which is unsubstituted.
  • L 1 is selected from a C6-C 4 oaryl group which is unsubstituted or substituted by at least one group E, preferably unsubstituted, or from a Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E, preferably unsubstituted.
  • L 1 is selected from a C6-C 4 oaryl group which is unsubstituted or substituted by at least one group E and L 2 is selected from a Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E.
  • L 1 is selected from a C6-C 4 oaryl group which is unsubstituted or substituted by at least one group E, preferably unsubstituted
  • L 2 is selected from a Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E, preferably unsubstituted
  • L 3 is selected from a Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E, preferably unsubstituted.
  • R 14 can be selected from the group as mentioned above.
  • R 14 is hydrogen.
  • the present invention relates to the compounds according to the present invention, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently of each other selected from H, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , wherein L 1 , L 2 , L 3 and L 4 are independently of each other selected from a C6-C 4 oaryl group which is unsubstituted or substituted by at least one group E or Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E, and R 14 is independently of each other selected from H or a Ci-C2salkyl group which unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, wherein o, p, q, r, E
  • the present invention relates to compounds according to the present invention, wherein R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , if present, are independently of each other selected from H, a C6-C 4 oaryl group which is unsubstituted or substituted by at least one group E or a C1-C24 N-comprising heteroaryl group which is unsubstituted or substituted by at least one group E, and
  • R 2 is selected from a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , wherein L 1 , L 2 , L 3 and L 4 are independently of each other selected from a C6-C4oaryl group which is unsubstituted or substituted by at least one group E or Ci-C24heteroaryl group which is unsubstituted or substituted by at least one group E, and R 14 is independently of each other selected from H or a Ci-C2salkyl group which unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, wherein L 1 , L 2 , L 3 , L 4 , o, p, q, r, E and D have the meanings and preferred meanings as mentioned above.
  • the present invention relates to compounds according to the present in- vention, wherein R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , if present, are H and
  • R 2 is selected from a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , wherein L 1 , L 2 , L 3 and L 4 are independently of each other selected from a C6-C4oaryl group which is unsubstituted or substituted by at least one group E or Ci-C24heteroaryl group which is unsubstituted or substituted by at least one group E, and R 14 is independently of each other selected from H or a Ci-C2salkyl group which unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, wherein L 1 , L 2 , L 3 , L 4 , o, p, q, r, E and D have the meanings and preferred mean- ings as mentioned above.
  • At least two of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 if present at adjacent carbon atoms, together form at least one C6-Cisaryl or Ci-Cisheteroaryl ring or ring system.
  • two of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 if present at adjacent carbon atoms, together form one C6-Cisaryl or Ci-Cisheteroaryl ring or ring system.
  • further two of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 if present at adjacent carbon atoms, may together form at least one further C6-Cisaryl or Ci-Cisheteroaryl ring or ring system.
  • two of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 in each case, if present at adjacent carbon atoms, can together form at least one, two, three or four C6-Cisaryl or Ci-Cisheteroaryl rings or ring systems.
  • C6-Cisaryl or Ci-Cisheteroaryl rings or ring systems are for example fused phenylene or naphthylene rings, five or six membered fused Ci-Cisheteroarylene rings or ringsystems.
  • the present invention relates to compounds according to the present invention, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , if present, are independently of each other selected from H or a N-heteroaryl group according to general formula (XI I):
  • n is an integer of 0 to 8
  • m is an integer of 0 to 4
  • M is a C6-C40 arylene group which is unsubstituted or substituted by at least one group E, a Ci- C24heteroarylene group which is unsubstituted or substituted by at least one group E or a C1-C25 alkylene group which unsubstituted or substituted by at least one group E and/or interrupted by at least one group D,
  • R 26 is independently of each other selected from E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C25alkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, wherein o, p, q, r, L 1 , L 2 , L 3 , L 4 , R 14 > E and D have the meanings as mentioned above, or at least two of R 26 , if present at adjacent carbon atoms, may form at least one five or six mem- bered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring or ring system, to which at least one further aromatic and /or heteroaromatic ring or ringsystem may be fused.
  • N-heteroaryl group according to general formula (XII) is a very specific embodiment of the group of formula -(L 1 ) 0 -(L 2 ) P - (L 3 ) q -(L 4 )rR 14 as defined above.
  • N-heteroaryl group according to general formula (XI I) is defined as follows.
  • n is an integer of 0 to 8, wherein n describes the number of substituents R 26 present. If n is 0, no substituent R 26 is present, but all eight positions at the fused phenyl rings carry a hydrogen. In case that at least one substituent R 26 is present at least one hydrogen at the fused phenyl rings is replaced by this at least one substituent R 26 .
  • At least two of R 26 may form at least one five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring or ring system, to which at least one further aromatic or heteroaromatic ring or ringsystem may be fused to
  • the at least at least one further aromatic ring or ringsystem may comprise 5 to 40 carbon atoms
  • the at least at least one further heteroaromatic ring or ringsystem may comprise 1 to 40 carbon atoms and heteroatoms like N , O, P or S.
  • At least two of R 26 may form at least one five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring or ring system, in combination with further substituents R 26 selected from E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C2salkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, wherein o, p, q, r, L 1 , L 2 , L 3 , L 4 , R 14 ' E and D have the meanings as mentioned above, or at least two of R 26 , if present at adjacent carbon atoms, may form at least one five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaro
  • At least two substituents R 26 may form at least one five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring or ring system, i.e.
  • substituents that are present at adjacent carbon atoms may form a five or six membered, substituted or unsubstituted, saturat- ed, unsaturated, aromatic or heteroaromatic ring or ring system
  • further substituents R 26 that are present at further two adjacent carbon atoms, may form a further five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring or ring system.
  • one, two, three or four, preferably one or two, five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring(s) or ring system(s) may be present at the N-heteroaryl group according to general formula (XII).
  • At least two substituents R 26 may form a structure according to general formula (XVII):
  • R 53 , R 54 , R 55 and R 56 are independently of each other selected from H, E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C2salkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, wherein o, p, q, r, L 1 , L 2 , L 3 , L 4 , R 14 ' E and D have the meanings as mentioned above, preferably H, or at least two of R 53 , R 54 , R 55 or R 56 , if present at adjacent carbon atoms, may form at least one five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or het- eroaromatic ring or ring system, to which further aromatic and /or heteroaromatic rings or ring systems may be fused.
  • two of R 26 if present at adjacent carbon atoms, form a fused phenyl ring, a fused naphthyl ring, a fused phenanthryl ring, a fused carbazole ring, a fused dibenzofuran ring, a fused dibenzothiophene ring, a fused fluorene ring, and a fused fluoranthene ring, wherein, if a fused fluoranthene ring is present it is built up by three of R 26 .
  • N-heteroaryl group according to general formula (XII) corresponds to the heteroaryl group according to the following formula (XIII):
  • n 0 to 4
  • R 28 , R 29 , R 30 , R 31 , R 37 and R 38 are independently of each other selected from H, E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C2salkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, preferably H, phenyl, biphenyl, or at least two of R 28 , R 29 , R 30 , R 31 , R 37 or R 38 , if present at adjacent carbon atoms, together form at least one C6-Cisaryl or Ci-Cisheteroaryl ring or ring
  • Q and T are independently of each other selected from direct bond, S, O, SiR 32 R 33 , CR 34 R 35 or N R 36 , wherein R 32 and R 33 are independently of each other H , a Ci-Cisalkyl group, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group, preferably H , a C6- Cisaryl group which is unsubstituted or a Ci-Cisalkyl group, preferably H , methyl, ethyl, or phenyl,
  • R 34 and R 35 are independently of each other H , E, a C6-C2 4 aryl group which is unsubstituted or substituted by at least one group E, Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E, a Ci-C2salkyl group which unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C2saralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, or spiro group, wherein R 34 and R 35 together form a five or six membered, substituted or unsubstituted, aliphatic ring, preferably H , methyl, ethyl, phenyl, or spiro group, wherein R 34 and R 35 together form a five or
  • Q is direct bond
  • T is NR 36
  • R 36 is phenyl
  • R 37 and R 38 are H
  • m is 0,
  • n is 0 and R 28 , R 29 , R 30 and R 31 are H.
  • heteroaryl group according to general formula (XIII) corresponds to general formula (XIV):
  • R 39 , R 40 , R 41 , R 42 are independently of each other selected from H, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O, preferably H, a C6-Cisaryl group which is unsubstituted or a Ci-Cisalkyl group, preferably R 39 , R 40 , R 41 and R 42 are H.
  • Q is direct bond
  • T is S
  • R 39 , R 40 , R 41 and R 42 are H
  • m is 0 or 1
  • n is 0 and R 28 , R 29 , R 30 and R 31 are H.
  • Q is direct bond
  • T is NR 36
  • R 36 is phenyl
  • R 39 , R 40 , R 41 and R 42 are H
  • m is 0,
  • n is 0 and R 28 , R 29 , R 30 and R 31 are H.
  • Q is direct bond
  • T is CR 34 R 35 , R 34 and R 35 are methyl
  • R 39 , R 40 , R 41 and R 42 are H
  • m is 0,
  • n is 0 and R 28 , R 29 , R 30 and R 31 are H.
  • Q is S
  • T is direct bond
  • R 39 , R 40 , R 41 and R 42 are H
  • m is 0, n is 0 and R 28 , R 29 , R 30 and R 31 are H.
  • Q is NR 36
  • T is direct bond
  • R 36 is phenyl
  • R 39 , R 40 , R 41 and R 42 are H
  • m is 0,
  • n is 0 and R 28 , R 29 , R 30 and R 31 are H.
  • N-heteroaryl group according to general formula (XII) corresponds to the heteroaryl group according to the follow- ing formula (XV):
  • n 0 to 4
  • R 28 , R 29 , R 30 , R 31 , R 43 and R 44 are independently of each other selected from H, E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C2salkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, preferably H, or at least two of R 28 , R 29 , R 30 or R 31 , if present at adjacent carbon atoms, together form at least one C6-Cisaryl or Ci-Cisheteroaryl ring or ring system, and Q and T are independently of each other selected from direct bond, S,
  • R 34 and R 35 are independently of each other H, E, a C6-C2 4 aryl group which is unsubstituted or substituted by at least one group E, Ci-C2 4 heteroaryl group which is unsubstituted or substituted by at least one group E, a Ci-C2salkyl group which unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, or spiro group, wherein R 34 and R 35 together form a five or six membered, substituted or unsubstituted, aliphatic ring, preferably H, ethyl, ethyl, phenyl, and spiro group, wherein R 34 and R 35 together form a five or
  • R 36 is H, a C6-Cisaryl group which is unsubstituted or substituted by at least one Ci-Cisalkyl group or at least one Ci-Cisalkoxy group, a Ci-Cisalkyl group or a Ci-Cisalkyl group, which is interrupted by at least one O, preferably H, a C6-Cisaryl group which is unsubstituted or a Ci- Cisalkyl group, for example phenyl, wherein D and E have the same meanings as mentioned above.
  • m is 0, n is 0, R 28 , R 29 , R 30 , R 31 , R 43 and R 44 are H, Q is a direct bond, T is CR 34 R 35 , R 34 and R 35 are methyl.
  • m is 0, n is 2, R 28 , R 29 , R 30 , R 31 , R 43 and R 44 are H, two R 26 that are present at adjacent carbon atoms together form a fused phenyl ring, which is preferably present in position of R 30 and R 31 , Q is a direct bond, T is CR 34 R 35 , R 34 and R 35 are methyl.
  • R 26 may correspond to the following formula (XVI):
  • R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 and R 52 are independently of each other H, E, a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , a Ci-C2salkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C2saralkyl which is unsubsti- tuted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E, or at least two of R 46 , R 47 , R 49 , R 50 , R 51 or R 52 , if present at adjacent carbon atoms, together form at least one C6-Cisaryl or Ci-Cisheteroaryl ring or ring system, wherein E
  • R 45 , R 46 , R 47 , R 49 , R 50 , R 51 and R 52 are independently of each other H , E, a unsubstituted C6-Cisaryl group or a C6-Cisaryl group substituted with at least one group E, or a Ci-C25alkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, preferably H , phenyl, biphenyl, naphthyl, phenanthryl or dimethylflu- orenyl.
  • R 48 is particularly preferred H , a unsubstituted C6-Cisaryl group or a C6-Cisaryl group substituted with at least one group E, preferably phenyl, biphenyl or naphthyl.
  • R 46 , R 47 , R 49 , R 50 , R 51 or R 52 are preferably present at adjacent carbon atoms, together form at least one C6-Cisaryl or Ci-Cisheteroaryl ring or ring system, most preferably a fused phenyl ring.
  • R 45 , R 46 , R 47 , R 49 , R 50 , R 51 and R 52 are H and R 48 is phenyl.
  • R 49 and R 50 are H , R 51 and R 52 form a fused phenyl ring and R 48 is phenyl.
  • m is an integer of 0 to 4, wherein m describes the number of groups M present. If m is 0, no group M is present, but the N-heteroaryl group according to general formula (XII) is directly attached to carbon atom within the skeleton of the compound of general formula (I).
  • m is 0, 1 , 2 or 3, more preferably, m is 0 or 1.
  • M is a C6-C40 arylene group which is unsubstituted, a Ci-C24heteroarylene group which is unsubstituted or a Ci-C2s alkylene group which unsubstituted.
  • M is a C6-C18 arylene group which is unsubstituted, most preferably a phenylene group.
  • R 26 is independently of each other selected from a group of formula -(L 1 ) 0 -(L 2 ) p -(L 3 ) q - (L 4 )rR 14 , wherein o, p, q, r, L 1 , L 2 , L 3 , L 4 and R 14 have the meanings and preferred meanings as mentioned above.
  • m is 0, and at least two of R 26 , if present at adjacent carbon atoms, form at least one five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring or ring system, without further substituents R 26 .
  • m is 1
  • M is M is a C6-C4oarylene group which is unsubstituted or substituted by at least one group E, preferably phenylene, and at least two of R 26 , if present at adjacent carbon atoms, form a five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring or ring system, without further substituents R 26 .
  • the present invention therefore preferably relates the compound according to the present invention, wherein m is 1 , M is a C6-C4oarylene group which is unsubstituted or substituted by at least one group E, preferably phenylene, and at least two of R 26 , if present at adjacent carbon atoms, form a five or six membered, substituted or unsubstituted, saturated, unsaturated, aromatic or heteroaromatic ring, wherein E has the meanings as mentioned above.
  • the present invention further preferably relates to the compound according to the present invention, wherein R 2 is a N-heteroaryl group according to general formula (XI I) as defined above.
  • the present invention further preferably relates to the compound according to the present invention, wherein R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are H and R 2 is a N-heteroaryl group according to general formula (XII) as defined above.
  • R 11 are independently of each other selected from H , E, a group of formula -(L 1 ) 0 - (L 2 )p-(L 3 )q-(L 4 )rR 14 , a Ci-C25alkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by at least one group D, a C 7 -C25aralkyl which is unsubstituted or substituted by at least one group E, a C5-Ci2cycloalkyl group which is unsubstituted or substituted by at least one group E.
  • R 11 is a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , wherein general and preferred embodiments of this group are mentioned above. Particularly preferred, R 11 is a group of formula -(L 1 ) 0 -(L 2 )p-(L 3 )q-(L 4 ) r R 14 , wherein o is 1 , p, q and r are 0 and L 1 is independently of each other selected from a C6-C4oaryl group which is unsubstituted or substituted by at least one group E or Ci-C24heteroaryl group which is unsubstituted or substituted by at least one group E, and R 14 is H . Most preferably, R 11 is phenyl.
  • X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 can independently of each other be N , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 or CR 10 , wherein R 4 to R 10 have the same meanings as mentioned above.
  • non of X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 is N . i.e. beside X 1 and/or X 3 , optionally Y, and optionally N present in any substituent at X 1 , X 3 or Y, no further N atoms are present in the molecule.
  • the present invention preferably relates to compounds according to the present invention, wherein X 2 is CR 2 , X 4 is CR 4 , X 5 is CR 5 , X 6 is CR 6 , X 7 is CR 7 , X 8 is CR 8 , X 9 is CR 9 andX 10 is CR 10 , wherein R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 have the meanings as mentioned above.
  • the present invention therefore preferably relates to compounds according to the following formulae (lid), (lie) and (llf):
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 have the same meanings as mentioned above.
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are H and R 2 has the meanings as mentioned above.
  • the present invention preferably relates to compounds according to the following general formulae (I I Id), (I lie) and (I I If):
  • R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 have the same meanings as mentioned above.
  • R 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are H and R 2 has the meanings as mentioned above.
  • the present invention preferably relates to compounds according to the following general formulae (IVd), (IVe) and (IVf):
  • R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 have the same meanings as mentioned above.
  • R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are H and R 2 has the meanings as mentioned above.
  • the present invention relates to a compound of general formula (1 1 ):
  • R101 R102 R103 R104 R105 R106 R107 R108 , R 109 , R 110 , R 111 , R 112 , R 113 , R 114 , R 115 , and R 116 are independently of each other and selected from
  • a cycloalkyi group having 3 to 25 carbon atoms which is unsubstituted or substituted by at least one group G,
  • heterocyclic group having 3 to 30 ring atoms which is unsubstituted or substituted by at least one group G,
  • alkylthio group having 1 to 25 carbon atoms which is unsubstituted or substituted by at least one group G,
  • a mono-, di-, or tri-substituted silyl group wherein the substituent is selected from an alkyl group having 1 to 25 carbon atoms which is unsubstituted or substituted by at least one group G and an aryl group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by at least one group G,
  • a mono- or di-substituted amino group wherein the substituent is selected from an alkyl group having 1 to 25 carbon atoms which is unsubstituted or substituted by at least one group G and an aryl group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by at least one group G,
  • a substituted carbonyl group wherein the substituent is selected from an alkyl group having 1 to 25 carbon atoms which is unsubstituted or substituted by at least one group G and an aryl group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by at least one group G, and
  • R 120 and R 121 are independently of each other selected from an alkyl group having 1 to 25 carbon atoms which is unsubstituted or substituted by at least one group G, an aryl group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by at least one group G, and a heterocyclic group having 3 to 30 ring atoms which is unsubstituted or substituted by at least one group G.
  • Halogen is fluorine, chlorine, bromine and iodine, preferably fluorine.
  • Alkyl group having 1 to 25, preferably 1 to 18, more preferably 1 to 8 carbon atoms is linear or branched. Examples are a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, an octadecyl group, and a tetracosanyl group.
  • Preferred exas are a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, and an octadecyl group, and more preferred examples are a me- thyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group,
  • Alkenyl group having 2 to 25, preferably 2 to 18, more preferably 2 to 8 carbon atoms is linear or branched.
  • Examples are a vinyl group, a 2-propenyl group, an isopropenyl group, an allyl group, a butenyl group, a hexenyl group, and a decenyl group, preferably a vinyl group, a 2- propenyl group, an isopropenyl group and an allyl group, and more preferably a vinyl group and a 2-propenyl group.
  • Alkynyl group having 2 to 25, preferably 2 to 18, more preferably 2 to 8 carbon atoms is linear or branched. Examples are an ethynyl group, a propargyl group, and a 3-pentynyl group.
  • Cycloalkyl group having 3 to 25, preferably 3 to 10, more preferably 3 to 8 carbon atoms is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group, with a cyclopentyl group and a cyclohexyl group being preferred.
  • Alkoxy group having 1 to 25, preferably 1 to 18, more preferably 1 to 8 carbon atoms is linear or branched.
  • Examples are a methoxy, an ethoxy group, a n-propoxy group, an isopropoxy group, an n-butoxy group, a s-butoxy group, a tert-butoxy group, an amyloxy group, an isoamyloxy group, a t-amyloxy group, a heptyloxy group, an octyloxy group, an isooctyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, a tetradecyloxy group, a pentadecyloxy group, a hexadecyloxy group, a heptadecyloxy group and an octade- cyloxy group.
  • Preferred examples are
  • Aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms is a single ring group, a ring assembly group, or a fused ring group (fused aryl group) having 10 to 30, preferably 10 to 25, more preferably 10 to 18 ring carbon atoms.
  • Examples are a phenyl group, a naphthyl group, a biphenylyl group, a terphenylyl group, a quarterphenylyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phe- nanthryl group, a benzophenanthryl group, a phenalenyl group, a fluorenyl group, a 9,9'- spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a benzonaphthoflu- orenyl group, a picenyl group, a pentaphenyl group, a pentacenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a s-indaceny
  • Preferred example are a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, a benzotriphenylenyl group, a 9,9-dimethylfluorenyl group, and a 9,9- diphenylfluorenyl group.
  • Heterocyclic group having 3 to 30, preferably 3 to 24, more preferably 3 to 20 ring atoms includes at least one, preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 or 2 hetero atoms which may be the same or different, for example, a nitrogen atom, a sulfur atom, and an oxygen atom.
  • the heterocyclic group may be a non-aromatic heterocyclic group having 3 to 30, preferably 3 to 24, more preferably 3 to 20 ring atoms or an aromatic heterocyclic group (het- eroaryl group) having 5 to 30, preferably 5 to 24, more preferably 5 to 20 ring atoms, each being a single ring group, a ring assembly group, or a fused ring group.
  • non-aromatic heterocyclic group examples include an aziridinyl, an oxiranyl group, a thii- ranyl group, an imidazolidinyl group, an imidazolinyl group, an indolinyl group, an oxazolidinyl group, an oxazolinyl group, an oxetanyl group, an azetidinyl group, a thietanyl group, a dio- xanyl group, a dioxolanyl group, a thiazolinyl group, a piperazinyl group, a piperidinyl group, a tetrahydropyranyl group, a tetrahydrothiopyranyl group, a pyrazolidinyl group, a pyrazolinyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a tetrahydo
  • heteroaryl group examples include a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imida- zolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an iso- thiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an isobenzothiophenyl group, an indolizinyl group, a qui- nolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl
  • Aryloxy group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms includes the aryl portion which is selected from the aryl group mentioned above or its preferred examples, and preferably a phenoxy group, 1-naphthoxy group, or a 2-naphthoxy group.
  • Alkylthio group having 1 to 25, preferably 1 to 18, more preferably 1 to 8 carbon atoms include the alkyi portion which is selected from the alkyi group mentioned above, its preferred examples, or its more preferred examples, and preferably a methylthio group, an ethylthio group, a n- propylthio group, an isopropylthio group, a n-butylthio group, an isobutylthio group, a s-butylthio group, a t-butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, and an oc- tylthio group.
  • Mono-, di-, or tri-substituted silyl group has one to three substituents which are independently selected from the alkyi group mentioned and the aryl group mentioned above, for example, a monoalkylsilyl group, a dialkylsilyl group, a trialkylsilyl group, a monoarylsilyl group, a diarylsilyl group, a triarylsilyl group, an alkyldiarylsilyl group, and a dialkylarylsilyl group, with a monoalkylsilyl group, a dialkylsilyl group, a trialkylsilyl group, a monoarylsilyl group, a diarylsilyl group, and a triarylsilyl group being preferred and a trialkylsilyl group and a triarylsilyl group being more preferred.
  • Examples are a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a propyldimethylsilyl group, an isopropyldimethylsilyl group, a triphenylsilyl group, a phenyldime- thylsilyl group, a t-butyldiphenylsilyl group, and a tritolylsilyl group.
  • Mono- or di-substituted amino group has one or two substituents which are independently selected from the alkyl group mentioned above and the aryl group mentioned above, for example, a monoalkyl amino group, a monoarylamino group, a dialkylamino group, a diarylamino group, and a alkylarylamino group, preferably a methylamino group, an ethylamino group, a phenyla- mino group, a dimethylamino group, a diethylamino group, a methylethylamino group, a diphe- nylamino group, a dinaphthylamino group, and a phenylnaphthyl group.
  • Substituted carbonyl group has a substituent which is selected from the alkyl group mentioned above and the aryl group mentioned above, preferably a methylcarbonyl group, an ethylcarbon- yl group, and a phenylcarbonyl group.
  • Two selected from R 101 , R 102 , R 103 , and R 104 which are present at adjacent two ring carbon atoms, may together form a ring structure, preferably a five or six membered, aromatic or non- aromatic hydrocarbon ring or a five or six membered, aromatic or non-aromatic heterocyclic ring, which is unsubstituted or substituted by at least one group G, and to which a five or six membered, aromatic or non-aromatic hydrocarbon ring and/or a five or six membered, aromatic or non-aromatic heterocyclic ring may be fused.
  • two selected from R 101 , R 102 , R 103 , and R 104 which are present at adjacent two ring carbon atoms, do not form a ring structure.
  • R 105 , R 106 , R 107 , R 108 , R 109 , R 110 , R 111 , R 112 , R 113 , R 114 , R 115 , and R 116 do not form a ring structure.
  • R 110 , R 111 , R 112 , R 113 , R 114 , R 115 , and R 116 are preferably all hydrogen atoms.
  • G is independently of each other and selected from a halogen atom, a cyano group, an alkyl group having 1 to 25 carbon atoms, an alkenyl group having 2 to 25 carbon atoms, an alkynyl group having 2 to 25 carbon atoms, a cycloalkyl group having 3 to 25 carbon atoms, an alkoxy group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heterocy- die group having 3 to 30 ring atoms, an aryloxy group having 6 to 30 ring carbon atoms, an al- kylthio group having 1 to 25 carbon atoms, an arylthio group having 6 to 30 ring carbon atoms, a mono-, di-, or tri-substituted silyl group, wherein the substituent is selected from an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, a mono-, di-
  • L 100 of formula (1 1 ) is selected from a direct bond, an arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms which is unsubstituted or substituted by at least one group G, or a heteroarylene group having 5 to 30, preferably 5 to 25, more preferably
  • the arylene group is a group formed when one hydrogen atom is removed from the aryl group mentioned above with respect to R 101 to R 116 , for example, a phenylene group, a naphthylene group, and a biphenylene group, preferably a p-phenylene group, a m-phenylene group, a naphthalene-2,7-diyl group, a naphthalene-1 ,4-diyl group, and a biphenyl-4,4'-diyl group.
  • the heteroarylene group is a group formed when one hydrogen atom is removed from the het- eroaryl group mentioned above with respect to R 101 to R 116 , for example, an imidazolediyl group, a pyridinediyl group, a pyridazinediyl group, a pyradinediyl group, a pyrimidinediyl group, a trizainediyl group, a pyrrolediyl group, a frandiyl group, a thiophenediyl group, and a
  • L 100 is selected from a direct bond and the arylene group mentioned above.
  • n 100 is an integer of 1 to 4, preferably 1 to 3, more preferably 1 or 2, and still more preferably 1 .
  • n 100 is 1 and L 100 is the arylene group mentioned above.
  • n 100 is 1 and L 100 is a direct bond.
  • R 100 is selected from a hydrogen atom, an aryl group having 6 to 30 carbon atoms which is un- substituted or substituted by at least one group G, a heterocyclic group having 3 to 30 ring atoms which is unsubstituted or substituted by at least one group G, or an alkyl group having 1 to 25 carbon atoms which is unsubstituted or substituted by at least one group G, wherein said groups and G have the meanings mentioned above with respect to R 101 to R 116 .
  • R 100 is selected from the aryl group mentioned above and the heteroaryl group mentioned above.
  • the aryl group for R 100 is selected from a phenyl group, a biphenylyl group, a terphenylyl group, or a fused aryl group having 10 to 30, preferably 10 to 25, more preferably 10 to 18 ring carbon atoms which is unsubstituted or substituted by at least one group G.
  • fused aryl group examples include a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a ben- zophenanthryl group, a phenalenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a benzonaphthofluorenyl group, a picenyl group, a pentaphenyl group, a pentacenyl group, a pyrenyl group, a chrysenyl group, a ben- zochrysenyl group, a s-indacenyl group, an as-indacenyl group, a fluoranthenyl group, a benz
  • the aryl group for R 100 is selected from a phenyl, a biphenylyl group, and a fused aryl group having 10 to 30, for example, a naphthyl group, a phe- nanthrenyl group, a fluoranthenyl group, a triphenylenyl group, and a benzotriphenylenyl group.
  • the heteroaryl group for R 100 is selected from the het- eroaryl group mentioned above.
  • the heteroaryl group for R 100 is selected from a heteroaryl group comprising a nitrogen-comprising six membered ring, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group, to each of which at least one selected from a six membered, aromatic hydrocarbon ring, a five or six membered, non-aromatic hydrocarbon ring, a five or six membered, aromatic heterocyclic ring, and a five or six membered, non- aromatic heterocyclic ring may be fused to form, for example, a (benzo)naphtofuranyl group, a (benzo)naphthothiopenyl group, a benzocarbazolyl group, an indolocarbazolyl group, a (benzo- furano)carbazolyl group, and a (benzothieno)carbazolyl group.
  • These groups may be unsubsti- tut
  • the heteroaryl group comprising a nitrogen-comprising six membered ring is selected from a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a phenanthridinyl group, an acri- dinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazi- nyl group, an azatriphenylenyl group, and a diazatriphenylenyl group, each of which is un
  • heteroaryl group is a fused heteroaryl group
  • a free bond may present on any of the fused rings, for example, a quinazolinyl group may be a 2-, 4-, 5-, 6-, 7- or 8- quinazolinyl group which is unsubstituted or substituted by at least one group G.
  • the heteroaryl group comprising a nitrogen-comprising six membered ring is of general formula (12):
  • X 61 is CR 61 or a nitrogen atom
  • X 63 is CR 63 or a nitrogen atom
  • X 65 is CR 65 or a nitrogen atom
  • X 61 , X 63 , and X 65 is a nitrogen atom; one of R 61 , R 62 , R 63 , R 64 , R 65 , and R 66 is a direct bond to L 100 , and
  • the others are independently of each other and selected from a hydrogen atom and G, preferably selected from a hydrogen atom and the aryl group mentioned above, more preferably selected from a hydrogen atom, a phenyl group, a biphenylyl group, a naphthyl group, and a phe- nanthryl group; wherein
  • X 66 is selected from an oxygen atom, a sulfur atom, NR 69 , or CR 70 R 71 ;
  • R 69 is selected from an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 ring atom, and an alkyl group having 1 to 25 carbon atoms, each of which has the meaning mentioned above, preferably selected from the aryl group mentioned above, and more preferably a phenyl group;
  • R 70 and R 71 are independently of each other and selected from an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 ring atom, and an alkyl group having 1 to 25 carbon atoms, each of which has the meaning mentioned above, preferably selected from the aryl group mentioned above and the alkyl group mentioned above, and more preferably a phenyl group and a methyl group; and R 67 and R 68 are independently of each other and selected from a hydrogen atom and G, preferably a hydrogen atom; or R 67 and R 68 may together form a five or six membered, aromatic or non-aromatic hydrocarbon ring which is unsubstituted or substituted by at least one group G or a five or six membered, aromatic or non-aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G, to each of which a five or six membered, aromatic or non-aromatic hydrocarbon ring and/or a
  • R 72 , R 73 , R 74 , and R 75 are independently of each other and selected from a hydrogen atom and G; and two of R 72 , R 73 , R 74 , and R 75 , which are present at adjacent two ring carbon atoms, may together form a five or six membered, aromatic or non-aromatic hydrocarbon ring which is unsubstituted or substituted by at least one group G or a five or six membered, aromatic or non-aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G, to each of which a five or six membered, aromatic or non-aromatic hydrocarbon ring and/or a five or six membered, aromatic or non-aromatic heterocyclic ring may be fused; or
  • three of R 61 , R 62 , R 63 , R 64 , R 65 , and R 66 which are present at consecutive three ring carbon atoms, may together form a fused ring structure which comprises three fused rings each selected from a six membered, aromatic hydrocarbon ring which is unsubstituted or substituted by at least one group G, a five or six membered, non-aromatic hydrocarbon ring which is unsubstitut- ed or substituted by at least one group G, a five or six membered, aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G, and a five or six membered, non- aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G.
  • the heteroaryl group comprising a nitrogen-comprising six membered ring is of general formula (12) is a pyridinyl group, a pyrimidinyl group or a tria- zinyl group, each of which is unsubstituted or substituted by at least one group G.
  • heteroaryl group comprising a nitrogen-comprising six membered ring of general formula (12), wherein two of R 61 , R 62 , R 63 , R 64 , R 65 , and R 66 together forms a ring structure of formula (14), corresponds to general formula (15):
  • R 62 , R 63 , and R 66 are preferably selected from a hydrogen atom and the aryl group mentioned above, more preferably selected from a hydrogent atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group; and R 72 , R 73 , R 74 , and R 75 are preferably all hydrogen atoms.
  • formula (15) corresponds to formula (15a) or (15b), pref- erably (
  • R 62 , R 66 , R 72 , R 73 , R 74 , and R 75 have the meanings mentioned above.
  • R 62 and R 66 are preferably selected from a hydrogen atom and the aryl group mentioned above, more preferably selected from a hydrogent atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group; and
  • R 72 , R 73 , R 74 , and R 75 are preferably all hydrogen atoms.
  • formula (15) also corresponds to general formulae (15c), (15d), (15e), (15f), (15g) and (15h):
  • R 72a R 72b , R 72c , and R 72d are independent of each other and selected from a hydrogen atom and G, preferably a hydrogen atom.
  • heteroaryl group comprising a nitrogen-comprising six membered ring of general formula (12), wherein two of R 61 , R 62 , R 63 , R 64 , R 65 , and R 66 together forms a ring structure of formula (13), wherein R 67 and R 68 together forms a five or six membered, aromatic or non-aromatic hydrocarbon ring, corresponds to general formula (16) or (17):
  • X 61 , X 63 , X 66 , R 62 , and R 66 have the meanings mentioned above, and R 76 , R 77 , R 78 , and R 79 are independent of each other and selected from a hydrogen atom and G, preferably a hydrogen atom.
  • formulae (16) and (17) correspond to general formulae (16a) and (16
  • X 61 , X 63 , X 66 , and R 66 have the meanings mentioned above, and R 76 , R 77 , R 78 , and R 79 are independent of each other and selected from a hydrogen atom and G, preferably a hydrogen atom.
  • R 66 is preferably selected from the aryl group mentioned above, more preferably a phenyl group.
  • formulae (16a) and (17b) correspond to general formulae (16b), (16c), (16d), (17b), (17c), and (17d):
  • R 66 has the meaning mentioned above, preferably selected from the aryl group mentioned above, more preferably a phenyl group; and R 70 , R 71 , R 76 , R 77 , R 78 , and R 79 are independent of each other and selected from a hydrogen atom and G, preferably a hydrogen atom.
  • heteroaryl group comprising a nitrogen-comprising six membered ring of general formula
  • R 79 are independent of each other and selected from a hydrogen atom and G.
  • X 66 of formulae (18) to (23) is an oxygen atom, a sulfur atom, or a C(CH 3 ) 2
  • R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , and R 78 of formulae (18) to (23) are all hydrogen atoms.
  • R 61 , R 62 , R 63 , R 64 , R 65 , and R 66 of the heteroaryl group comprising a nitrogen- comprising six membered ring of general formula (12) may together form a fused ring structure which comprises three fused rings each selected from a six membered, aromatic hydrocarbon ring which is unsubstituted or substituted by at least one group G, a five or six membered, non- aromatic hydrocarbon ring which is unsubstituted or substituted by at least one group G, a five or six membered, aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G, and a five or six membered, non-aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G.
  • the heteroaryl group comprising a nitrogen-comprising six membered ring of general formula (12), wherein three of R 61 , R 62 , R 63 , R 64 , R 65 , and R 66 together form a fused ring structure which comprises three fused rings, corresponds to formula (24):
  • X 61 and X 65 have the meanings mentioned above, and F1 , F2, and F3 are independent of each other and selected from a six membered, aromatic hydrocarbon ring which is unsubsti- tuted or substituted by at least one group G, a five or six membered, non-aromatic hydrocarbon ring which is unsubstituted or substituted by at least one group G, a five or six membered, aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G, and a five or six membered, non-aromatic heterocyclic ring which is unsubstituted or substituted by at least one group G.
  • the six membered, aromatic hydrocarbon ring is a benzene ring; the five or six membered, non-aromatic hydrocarbon ring is a cyclopentane ring or a cyclohex- ane ring; the five or six membered, aromatic heterocyclic ring is selected from the corresponding rings of the heteroaryl group mentioned above; and the five or six membered, non-aromatic hydrocarbon ring is selected from the corresponding rings of the non-aromatic heterocyclic group mentioned above.
  • formula 24 corresponds to formula (25):
  • X 61 and X 65 have the meanings mentioned above,
  • Y is selected from an oxygen atom, a sulfur atom, NR 87 , and CR 88 R 89 ;
  • R 87 is selected from an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 ring atom, and an alkyl group having 1 to 25 carbon atoms, each of which has the meaning mentioned above, preferably selected from the aryl group mentioned above, and more preferably a phenyl group;
  • R 88 and R 89 are independently of each other and selected from an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 ring atom, or an alkyl group having 1 to 25 car ⁇ bon atoms, each of which has the meaning mentioned above, preferably selected from the aryl group mentioned above and the alkyl group mentioned above, and more preferably selected from a phenyl group and a methyl group;
  • X 80 is CR 80 or a nitrogen atom
  • X 81 is CR 81 or a nitrogen atom
  • X 82 is CR 82 or a nitrogen atom
  • X 83 is CR 83 or a nitrogen atom
  • X 84 is CR 84 or a nitrogen atom
  • X 85 is CR 85 or a nitrogen atom
  • X 86 is CR 86 or a nitrogen atom
  • R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , and R 86 are independently of each other and selected from a hydro ⁇ gen atom and G, preferably
  • X 80 is CR 80
  • X 81 is CR 81
  • X 82 is CR 82
  • X 83 is CR 83
  • X 84 is CR 84
  • X 85 is CR 85
  • X 86 is CR 86
  • R 80
  • R 81 , R 82 , R 83 , R 84 , R 85 , and R 86 are each hydrogen atom.
  • formulae (24) and (25) correspond to any of formu- lae (26) to (29):
  • formulae (24) to (29) correspond to any of formulae (30) to (33):
  • the compound of formula (1 1 ) can be synthesized according to the methods described in the synthesis examples below or modified methods thereof.
  • the compounds according to general formulae (I) and (1 1 ) are particularly suitable for use in applications in which charge carrier conductivity is required, especially for use in organic electronics applications, for example selected from switching elements such as organic transistors, e.g. organic FETs and organic TFTs, organic solar cells and organic light- emitting diodes (OLEDs).
  • switching elements such as organic transistors, e.g. organic FETs and organic TFTs, organic solar cells and organic light- emitting diodes (OLEDs).
  • the present invention therefore also relates to an electronic device comprising at least one compound according to the present invention.
  • the organic transistor generally includes a semiconductor layer formed from an organic layer with charge transport capacity; a gate electrode formed from a conductive layer; and an insulating layer introduced between the semiconductor layer and the conductive layer. A source electrode and a drain electrode are mounted on this arrangement in order thus to produce the transistor element.
  • further layers known to those skilled in the art may be present in the organic transistor.
  • the layers with charge transport capacity may comprise the compounds according to general formulae (I) and (1 1 ) according to the present invention.
  • the organic solar cell generally comprises an organic layer present between two plate-type electrodes arranged in parallel.
  • the organic layer may be configured on a comb-type electrode.
  • at least one electrode is preferably formed from a transpar- ent electrode, for example an ITO electrode or a fluorine-doped tin oxide electrode.
  • the organic layer is formed from two sublayers, i.e. a layer with p-type semiconductor properties or hole transport capacity, and a layer formed with n-type semiconductor properties or charge transport capacity.
  • the layers with charge transport capacity may comprise a compound according to general formulae (I) and (1 1 ) according to the present invention.
  • a charge transport material for example as a hole transport material and/or as an electron transporting material, charge and/or exciton blocking material, particularly preferably as a host material or as an electron transporting material.
  • the present invention therefore preferably relates to the electronic device according to the present invention, preferably an organic electroluminescence device, more preferably an organic light emitting diode (OLED), comprising a cathode, an anode, and a plurality of organic layers provided between the cathode and the anode, the organic layers comprising an emitting layer comprising the at least one compound of general formulae (I) and (1 1 ), preferably as a host material, a charge transporting material, charge and/or exciton blocking material, particularly preferably as a host material or as an electron transporting material.
  • OLED organic light emitting diode
  • the compounds according to general formulae (I) and (1 1 ) are preferably suitable in OLEDs as host material, preferably in combination with a red phosphorescence emitter. Further preferred, the compounds according to general formulae (I) and (1 1 ) are particularly suitable in OLEDs as an electron transporting material, preferably in a light-emitting layer, especially in combination with preferably a blue fluorescence emitter, and preferably in an electron transport layer.
  • the present invention therefore preferably relates to the use of a compound according to gen- eral formulae (I) and (1 1 ) as defined above in an electronic device, preferably in an electroluminescence device, particularly preferably in an organic light emitting diode (OLED), preferably in an emitting layer, as a host material, a charge transporting material, for example as a hole transport material or an electron transport material, preferably as an electron transporting material, as a charge and/or exciton blocking material, preferably as a host material or an electron transporting material.
  • OLED organic light emitting diode
  • inventive compounds according to general formulae (I) and (1 1 ) are suitable especially for use as matrix and/or charge transport and/or charge blocking materials for green, red and yellow, preferably green and red, more preferably red emitters.
  • inventive compounds according to general formulae (I) and (1 1 ) are further suitable especially for use as electron transporting material for blue emitters.
  • the compounds according to general formulae (I) and (1 1 ) can be used as conduc- tor/complementary materials in organic electronics applications selected from switching elements and organic solar cells. According to the present application, the terms matrix and host are used interchangeable.
  • an emitter material with at least one matrix material of the compound according to general formulae (I) and (1 1 ) and one or more, preferably one, further matrix materials (co-host). This may achieve a high quantum efficiency, low driving voltage and/or long lifetime of these devices.
  • the compounds according to general formulae (I) and (1 1 ) are used as host materials, preferably in emitting layers comprising red light-emitting compounds. According to this embodiment, preferably no further host material is present in the light-emitting layer.
  • the compounds according to general formulae (I) and (1 1 ) are used as host materials, preferably in emitting layers comprising green light-emitting compounds.
  • the compounds according to the present invention are preferably used in the presence of at least one further host ma- terial, i.e. as a co-host. Further host materials are mentioned in the following.
  • the compounds according to general formulae (I) and (1 1 ) are present in two or three of the following layers: in the light-emitting layer (preferably as host material) and/or in the transport layer (as electron transport material).
  • a compound according to general formulae (I) and (1 1 ) is used as matrix (host) material in an emission layer and additionally as electron transport material, owing to the chemical identity or similarity of the materials, an improved interface between the emission layer and the adjacent material, which can lead to a decrease in the voltage with equal luminance and to an ex- tension of the lifetime of the OLED.
  • the use of the same material as electron transport material and/or as matrix of an emission layer allows the production process of an OLED to be simplified, since the same source can be used for the vapor deposition process of the material of one of the compounds of the formula the compound according to general formulae (I) and (1 1 ).
  • a charge transporting material for example as a hole transport material or an electron transport material, preferably as an electron transporting material, and/or exciton blocking material, particularly preferably as a host material or as an electron transporting material.
  • the present invention therefore preferably relates to the electronic device, preferably an organic electroluminescence device, more preferably an organic light emitting diode (OLED), according to the present invention, comprising a cathode, an anode, and a plurality of organic layers provided between the cathode and the anode, the organic layers comprising an emitting layer comprising the at least one compound of general formula (I) or (1 1 ), preferably as a host material, a charge transporting material, for example as a hole transport material or an electron transport material, preferably as an electron transporting material, and/or exciton blocking material, particularly preferably as a host material or as an electron transporting material.
  • OLED organic light emitting diode
  • the present invention provides an organic light-emitting diode (OLED) comprising an anode and a cathode and a light-emitting layer arranged between the anode and the cathode, and if appropriate at least one further layer selected from the group consisting of at least one blocking layer for holes/excitons, at least one blocking layer for electrons/excitons, at least one hole injection layer, at least one hole transport layer, at least one electron injection layer and at least one electron transport layer, wherein the at least one compound according to general formula (I) or (1 1 ) is present in the light-emitting layer and/or in at least one of the further layers.
  • the at least one compound according to general formula (I) or (1 1 ) is preferably present in the light-emitting layer and/or hole/exciton blocking layer and/or the charge blocking layer, i.e. the electron or hole transport layer.
  • At least one compound according to general formulae (I) and (1 1 ) is used as electron transport material.
  • Examples of preferred compounds according to general formulae (I) and (11 ) are shown above.
  • At least one compound of general formulae (I) and (1 1 ) is used as charge/exciton blocker material. Examples of preferred compounds according to general formulae (I) and (1 1 ) are shown above.
  • the present application further relates to a light-emitting layer, preferably present in an electron- ic device, more preferably in an electroluminescence device, particularly preferably in an organic light emitting diode (OLED), comprising at least one compound of general formula (I) or (1 1 ) as defined above, preferably as host material or co-host material. Examples of preferred compounds according to general formulae (I) and (1 1 ) are shown above.
  • the electronic device according to the present invention is an organic light emitting diode (OLED).
  • OLED organic light emitting diode
  • the inventive organic light-emitting diode thus generally has the following structure: an anode (a) and a cathode (i) and a light-emitting layer (e) arranged between the anode (a) and the cathode (i).
  • inventive OLED may, for example - in a preferred embodiment - be formed from the following layers:
  • Layer sequences different than the aforementioned structure are also possible, and are known to those skilled in the art.
  • the OLED does not have all of the layers mentioned; for example, an OLED with layers (a) (anode), (e) (light-emitting layer) and (i) (cathode) is likewise suitable, in which case the functions of the layers (c) (hole transport layer) and (f) (blocking layer for holes/excitons) and (g) (electron transport layer) are assumed by the adjacent layers.
  • OLEDs which have layers (a), (c), (e) and (i), or layers (a), (e), (f), (g) and (i), are likewise suitable.
  • the OLEDs may have a blocking layer for electrons/excitons (d) between the hole transport layer (c) and the light-emitting layer (e).
  • a plurality of the aforementioned functions are combined in one layer and are assumed, for example, by a single material present in this layer.
  • a material used in the hole transport layer in one embodiment, may simultaneously block excitons and/or electrons.
  • the individual layers of the OLED among those specified above may in turn be formed from two or more layers.
  • the hole transport layer may be formed from a layer into which holes are injected from the electrode, and a layer which transports the holes away from the hole-injecting layer into the light-emitting layer.
  • the electron transport layer may likewise consist of a plurality of layers, for example a layer in which electrons are injected by the electrode, and a layer which receives electrons from the electron injection layer and transports them into the light-emitting layer.
  • These layers mentioned are each selected according to factors such as energy level, thermal resistance and charge carrier mobility, and also energy difference of the layers specified with the organic layers or the metal electrodes.
  • the person skilled in the art is capable of selecting the structure of the OLEDs such that it is matched optimally to the organic compounds used in accordance with the invention.
  • the OLED according to the present invention comprises in this order: (a) an anode,
  • the anode is an electrode which provides positive charge carriers. It may be composed, for example, of materials which comprise a metal, a mixture of different metals, a metal alloy, a metal oxide or a mixture of different metal oxides. Alternatively, the anode may be a conductive polymer. Suitable metals comprise the metals of groups 1 1 , 4, 5 and 6 of the Periodic Table of the Elements, and also the transition metals of groups 8 to 10. When the anode is to be transparent, mixed metal oxides of groups 12, 13 and 14 of the Periodic Table of the Elements are generally used, for example indium tin oxide (ITO). It is likewise possible that the anode (a) comprises an organic material, for example polyaniline, as described, for example, in Nature, Vol.
  • Preferred anode materials include conductive metal oxides, such as indium tin oxide (ITO) and indium zinc oxide (IZO), aluminum zinc oxide (AlZnO), and metals.
  • Anode (and substrate) may be sufficiently transparent to create a bottom- emitting device.
  • a preferred transparent substrate and anode combination is commercially available ITO (anode) deposited on glass or plastic (substrate).
  • a reflective anode may be preferred for some top-emitting devices, to increase the amount of light emitted from the top of the device. At least either the anode or the cathode should be at least partly transparent in order to be able to emit the light formed. Other anode materials and structures may be used.
  • injection layers are comprised of a material that may improve the injection of charge carriers from one layer, such as an electrode or a charge generating layer, into an adjacent organic layer. Injection layers may also perform a charge transport function.
  • the hole injection layer may be any layer that improves the injection of holes from anode into an adjacent organic layer.
  • a hole injection layer may comprise a solution deposited material, such as a spin-coated polymer, or it may be a vapor deposited small molecule material, such as, for example, CuPc or MTDATA.
  • Polymeric hole-injection materials can be used such as poly(N-vinylcarbazole) (PVK), polythiophenes, polypyrrole, polyaniline, self-doping polymers, such as, for example, sulfonated poly(thiophene-3-[2[(2-methoxyethoxy)ethoxy]-2,5-diyl) (Plexcore ® OC Conducting Inks commercially available from Plextronics), and copolymers such as poly(3,4- ethylenedioxythiophene)/poly(4-styrenesulfonate) also called PEDOT/PSS.
  • PVK poly(N-vinylcarbazole)
  • polythiophenes polypyrrole
  • polyaniline polyaniline
  • self-doping polymers such as, for example, sulfonated poly(thiophene-3-[2[(2-methoxyethoxy)ethoxy]-2,5-d
  • An example for a suitable hole injection material is: (see also hole-transporting molecules)
  • the OLED according to the present invention comprises at least one compound according to general formulae (I) and (1 1 ) or their preferred embodiments as a charge transporting material, preferably as a hole transporting layer.
  • a charge transporting material preferably as a hole transporting layer.
  • hole transporting molecules or polymers may be used as the hole transport material.
  • Suitable hole transport materials for layer (c) of the inventive OLED are disclosed, for example, in Kirk- Othmer Encyclopedia of Chemical Technology, 4th Edition, Vol. 18, pages 837 to 860, 1996, US20070278938, US2008/0106190, US201 1/0163302 (triarylamines with
  • polymeric hole-injection materials can be used such as poly(N- vinylcarbazole) (PVK), polythiophenes, polypyrrole, polyaniline, self-doping polymers, such as, for example, sulfonated poly(thiophene-3-[2[(2-methoxyethoxy)ethoxy]-2,5-diyl) (Plexcore® OC Conducting Inks commercially available from Plextronics), and copolymers such as poly(3,4- ethylenedioxythiophene)/poly(4-styrenesulfonate) also called PEDOT/PSS.
  • PVK poly(N- vinylcarbazole)
  • polythiophenes polypyrrole
  • polyaniline polyaniline
  • self-doping polymers such as, for example, sulfonated poly(thiophene-3-[2[(2-methoxyethoxy)ethoxy]-2,5-diyl) (
  • Preferred examples of a material of the hole injecting layer are a porphyrin compound, an aromatic tertiary amine compound, or a styrylamine compound. Particularly preferable examples include an aromatic tertiary amine compound such as hexacyanohexaazatriphenylene (HAT).
  • HAT hexacyanohexaazatriphenylene
  • the hole-transporting layer may also be electronically doped in order to improve the transport properties of the materials used, in order firstly to make the layer thicknesses more generous (avoidance of pinholes/short circuits) and in order secondly to minimize the operating voltage of the device.
  • Electronic doping is known to those skilled in the art and is disclosed, for example, in W. Gao, A. Kahn, J. Appl. Phys., Vol. 94, 2003, 359 (p-doped organic layers); A. G. Werner, F. Li, K. Harada, M . Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., Vol. 82, No.
  • mixtures may, for example, be the following mixtures: mixtures of the abovementioned hole transport materials with at least one metal oxide, for example M0O2, M0O3, WO x , Re03 and/or V2O5, preferably M0O3 and/or Re03, more preferably M0O3, or mixtures comprising the aforementioned hole transport materials and one or more compounds selected from 7,7,8,8- tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 - TCNQ), 2,5-bis(2-hydroxyethoxy)-7,7,8,8-tetracyanoquinodimethane, bis(tetra-n- butylammonium)tetracyanodiphenoquinodimethane, 2,5-dimethyl-7,7,8,8- tetracyanoquinodimethane, tetracyanoethylene, 1 1 ,1 1 ,12
  • Blocking layers may be used to reduce the number of charge carriers (electrons or holes) and/or excitons that leave the emissive layer.
  • An electron/exciton blocking layer (d) may be disposed between the first emitting layer (e) and the hole transport layer (c), to block electrons from emitting layer (e) in the direction of hole transport layer (c). Blocking layers may also be used to block excitons from diffusing out of the emissive layer.
  • Suitable metal complexes for use as electron/exciton blocker material are, for example, carbene complexes as described in WO2005/019373A2, WO2006/056418A2, WO2005/1 13704,
  • At least one compound of general formulae (I) and (1 1 ) is present in the exciton blocking layer of the OLED according to the present invention.
  • the light emitting layer is an organic layer having a light emitting function and is formed from one or more layers, wherein one of the layers comprises a host material (first host material), optionally a second host material, and the light emitting material as described below.
  • the light emitting layer or layers other than that mentioned above contains or contain a host material and a dopant material when a doping system is employed.
  • the major function of the host material is to promote the recombination of electrons and holes and confine excitons in the light emitting layer.
  • the dopant material causes the excitons generated by recombination to emit light efficiently.
  • the major function of the host material is to confine the excitons generated on the dopant in the light emitting layer.
  • the light emitting layer may be made into a double dopant layer, in which two or more kinds of dopant materials having high quantum yield are used in combination and each dopant material emits light with its own color. For example, to obtain a yellow emission, a light emitting layer formed by co-depositing a host, a red-emitting dopant and a green-emitting dopant is used.
  • the light emitting layer may be different in the hole injection ability and the electron injection ability, and also in the hole transporting ability and the electron transporting ability each being expressed by mobility.
  • the light emitting layer is formed, for example, by a known method, such as a vapor deposition method, a spin coating method, and LB method.
  • the light emitting layer may be formed by making a solution of a binder, such as resin, and the material for the light emitting layer in a solvent into a thin film by a method such as spin coating.
  • the light emitting layer is preferably a molecular deposit film.
  • the molecular deposit film is a thin film formed by depositing a vaporized material or a film formed by solidifying a material in the state of solution or liquid.
  • the molecular deposit film can be distinguished from a thin film formed by LB method (molecular build-up film) by the differences in the assembly structures and higher order structures and the functional difference due to the structural differences.
  • the light-emitting layer (e) comprises at least one emitter material.
  • it may be a fluo- rescence or phosphorescence emitter, suitable emitter materials being known to those skilled in the art.
  • the at least one emitter material is preferably a phosphorescence emitter.
  • the emission wavelength of the phosphorescent dopant used in the light emitting layer is not particularly limited.
  • at least one of the phosphorescent dopants used in the light emitting layer has the peak of emission wavelength of in general 430 nm or longer and 780 nm or shorter, preferably 490 nm or longer and 700 nm or shorter and more preferably 490 nm or longer and 650 nm or shorter.
  • Most preferred are green emitter materials (490 to 570 nm).
  • red emitter materials (570 to 680 nm) are preferred.
  • the phosphorescent dopant is a compound which emits light by releasing the energy of excited triplet state and preferably a organometallic complex comprising at least one metal selected from Ir, Pt, Pd, Os, Au, Cu, Re, Rh and Ru and a ligand, although not particularly limited thereto as long as emitting light by releasing the energy of excited triplet state.
  • a ligand having an ortho metal bond is preferred.
  • a metal complex comprising a metal selected from Ir, Os, and Pt is preferred, with iridium complex, osmium complex, and platinum, particularly an ortho metallated complex thereof being more preferred, iridium complex and platinum complex being still more preferred, and an ortho metallated iridium complex being particularly preferred.
  • Suitable metal complexes for use in the inventive OLEDs, preferably as emitter material, are described, for example, in documents WO 02/60910 A1 , US 2001/0015432 A1 ,
  • WO 200612181 1 A1 WO 20070951 18 A2, WO 2007/1 15970, WO 2007/1 15981 , WO 2008/000727, WO2010129323, WO2010056669, WO10086089, US201 1/0057559,
  • metal complexes are the commercially available metal complexes tris(2- phenylpyridine)iridium(lll), iridium(lll) tris(2-(4-tolyl)pyridinato-N,C 2 '), bis(2- phenylpyridine)(acetylacetonato)iridium(lll), iridium(lll) tris(l -phenylisoquinoline), iridium(lll) bis(2,2'-benzothienyl)pyridinato-N,C 3 ')(acetylacetonate), tris(2-phenylquinoline)iridium(lll), iridium (I 11 ) bis(2-(4,6-difluorophenyl)pyridinato-N ,C 2 )picolinate, iridium(lll) bis(1 - phenylisoquinoline)(acetylacetonate), bis(2-phenylquinoline
  • red emitters are shown in WO 2008/109824. Preferred red emitters according to this d
  • the emitter materials may be used alone or in combination of two or more.
  • the light emitting layer may comprise at least one fluorescent, preferably blue, emitter.
  • fluorescent, preferably blue, emitter examples of preferred blue dopants that may be present in the light emitting layer of the OLED according to the present invention are polycyclic amine derivatives as mentioned in EP 2924029. Particularly preferred aromatic amine derivatives are selected from compounds according to the following formula (20):
  • Y is a substituted or unsubstituted fused aromatic hydrocarbon group including 10 to 50 ring carbon atoms.
  • Anoi, and Ano2 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic ring group including 5 to 50 ring atoms.
  • Y include the above-mentioned fused aryl group.
  • Y is preferably a substituted or unsubstituted anthryl group, a substituted or unsubstitued pyrenyl group or a substituted or unsubstituted chrysenyl group.
  • n is an integer of 1 to 4. It is preferred that n be an integer of 1 to 2.
  • the above-mentioned formula (20) is preferably one represented by the following formulas (21 ) to (24).
  • R e , R f and R g are independently a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted aralykyl group including 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted silyl group,
  • R e , R f and R g a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms can be given. More preferably, R e , R f and R g are a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or the like.
  • Ar2oi to Ar2ie are independently an aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.
  • Ar2oi to Ar2ie include a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group or the like.
  • the substit- uent of Ar2oi to Ar2ie an alkyl group, a cyano group and a substituted or unsubstituted silyl group can be given.
  • alkynyl group including 2 to 50 preferably 2 to 30, more preferably 2 to 20, particularly preferably 2 to 10.
  • a propargyl group, a 3-pentynyl group or the like can be given.
  • alkyl germanium group a methylhydrogermyl group, a trimethylgermyl group, a triethyl- germyl group, a tripropylgermyl group, a dimethyl-t-butylgermyl group or the like can be given.
  • aryl germanium group a phenyldihydrogermyl group, a diphenylhydrogermyl group, a triphenylgermyl group, a tritolylgermyl group, a trinaphthylgermyl group or the like can be given.
  • styrylamine compound and the styryldiamine compound those represented by the following formulas (17) and (18) are preferable.
  • Ar3oi is a k-valent group; a k-valent group corresponding to a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a stilbene group, a styrylaryl group and a distyrylaryl group.
  • Ar302 and Ar303 are independently an aryl group including 6 to 20 ring carbon atoms, and Ar3oi, Ar302 and Ar303 may be substituted.
  • k is an integer of 1 to 4, with an integer of 1 and 2 being preferable.
  • Any one of Ar3oi to Ar303 is a group including a styryl group. It is further preferred that at least one of Ar302 and Ar303 be substi- tuted by a styryl group.
  • the above-mentioned aryl group can be specifically given.
  • Preferable examples include a phenyl group, a naphthyl group, an an- thranyl group, a phenanthryl group, a terphenyl group or the like.
  • Ar304 to Ar306 are a v-valent substituted or unsubstituted aryl group including 6 to 40 ring carbon atoms, v is an integer of 1 to 4, with an integer of 1 and 2 being preferable.
  • aryl group including 6 to 40 ring carbon atoms in the formula (18) the above- mentioned aryl group can be specifically given.
  • a naphthyl group, an anthranyl group, a chrys- enyl group, a pyrenyl group or an aryl group represented by the formula (20) is preferable.
  • an alkyl group including 1 to 6 car- bon atoms, an alkoxy group including 1 to 6 carbon atoms, an aryl group including 6 to 40 ring carbon atoms, an amino group substituted by an aryl group including 6 to 40 ring carbon atoms, an ester group including an aryl group that includes 5 to 40 ring carbon atoms, an ester group including an alkyl group that includes 1 to 6 carbon atoms, a cyano group, a nitro group, a halogen atom or the like can be given.
  • the content of the emitter materials (dopants), preferably the phosphorescent emitter materials, in the light emitting layer is not particularly limited and selected according to the use of the device, and preferably 0.1 to 70% by mass, and more preferably 1 to 30% by mass. If being 0.1 % by mass or more, the amount of light emission is sufficient. If being 70% by mass or less, the concentration quenching can be avoided.
  • the further component in the emitting layer is usually one or more host material, which is preferably present in an amount of 30 to 99.9 % by mass, more preferably 70 to 99% by mass, wherein the sum of the emitter material(s) and the host material(s) is 100% by mass.
  • the light-emitting layer may comprise further components in addition to the emitter material.
  • a fluroescent dye may be present in the light-emitting layer in order to alter the emission color of the emitter material.
  • a matrix material can be used.
  • This matrix material may be a polymer, for example poly(N-vinylcarbazole) or pol- ysilane.
  • one or more phosphorescent hosts are employed as host material.
  • the phosphorescent host is a compound which confines the triplet energy of the phosphorescent dopant efficiently in the light emitting layer to cause the phosphorescent dopant to emit light efficiently.
  • the light-emitting layer is formed of at least one emitter material and of at least one of the matrix materials mentioned in this application.
  • the electronic device according to the present invention preferably the OLED according to the present invention, comprises at least one compound according to general formula (I) or (1 1 ) as matrix (host) material.
  • the light-emitting layer comprises at least one emitter material and at least two matrix materials, wherein one of the matrix materials is a compound according to general formula (I) or (1 1 ) and the other matrix material(s) is/are used as co-host(s). Suitable other host materials than the compounds of general formulae (I) and (1 1 ) (co-hosts) are mentioned below.
  • This embodiment is preferably realized with emitter materials that emit red light.
  • the light-emitting layer comprises at least one emitter material and a compound according to general formula (I) or (1 1 ) as a single matrix material. Examples of preferred compounds of general formulae (I) and (1 1 ) useful as single host material are shown above. This embodiment is preferably realized with emitter materials that emit red light.
  • the compounds according to general formulae (I) and (1 1 ) are suitable as single host material as well as host material, together with one or more further host materials (co-host). Suitable further host materials are mentioned below. "Further host materials" means in the sense of the present application, host materials different from the compounds of general formulae (I) and (1 1 ). However, it is also possible to use two or more different compounds of general formula (I) or (1 1 ) as host material in the light-emitting layer in an OLED of the present application.
  • the light-emitting layer is formed from 0.1 to 70% by weight, preferably 1 to 30% by weight, of at least one of the aforementioned emitter materials and 30 to 99.9% by weight, preferably 70 to 99% by weight, of at least one of the matrix materials mentioned in the specification - in one embodiment at least one compound according to general formulae (I) and (1 1 ) - where the sum total of the emitter material and of the matrix material adds up to 100% by weight.
  • the light-emitting layer comprises a compound of general formula (I) or (1 1 ) as matrix material, at least one further matrix material (co-host) and at least one emitter material.
  • the light-emitting layer is formed from 0.1 to 70% by weight, preferably 1 to 30% by weight, of the at least one emitter material and 30 to 99.9% by weight, preferably 70 to 99% by weight, of a compound according to general formula (I) or (1 1 ) and the further matrix material, where the sum total of the at least one emitter material, the further matrix material and of the compound of general formula (I) or (1 1 ) adds up to 100% by weight.
  • the content ratio of the compound according to general formula (I) or (1 1 ) as first host material and the second matrix material as co-host in the light emitting layer is not particularly limited and may be selected accordingly, and the ratio of first host material: second host material is preferably 1 :99 to 99:1 , more preferably 10:90 to 90:10, each based on mass.
  • host materials that may be used in the electronic device according to the present invention as single host materials, if the compounds according to the present invention are used as charge transporting material, i.e. as electron transporting material or hole transporting material.
  • the host materials that are mentioned in the following can also be used as second host materials, if the compounds according to general formula (I) or (1 1 ) are used as first host material and vice versa.
  • WO2007108459 H-1 to H-37
  • H-20 to H-22 and H-32 to H-37 most preferably H-20, H-32, H-36, H-37,
  • WO2008035571 A1 Host 1 to Host 6
  • JP2010135467 compounds 1 to 46 and Host-1 to Host- 39 and Host-43
  • WO2009008100 compounds No.1 to No.67 preferably No.3, No.4, No.7 to No. 12, No.55, No.59, No. 63 to No.67, more preferably No. 4, No. 8 to No. 12, No. 55, No. 59, No.64, No.65, and No. 67, WO2009008099 compounds No. 1 to No.
  • WO20081401 14 compounds 1 -1 to 1 -50, WO2008090912 compounds OC-7 to OC-36 and the polymers of Mo- 42 to Mo-51 , JP2008084913 H-1 to H-70, WO2007077810 compounds 1 to 44, preferably 1 , 2, 4-6, 8, 19-22, 26, 28-30, 32, 36, 39-44, WO201001830 the polymers of monomers 1 -1 to 1 -9, preferably of 1 -3, 1 -7, and 1 -9, WO2008029729 the (polymers of) compounds 1 -1 to 1 -36, WO20100443342 HS-1 to HS-101 and BH-1 to BH-17, preferably BH-1 to BH-17,
  • JP2008066569 the (co)polymers based on the monomers 1 -1 to 1 -16, WO2008029652 the (co)polymers based on the monomers 1-1 to 1 -52, WO20071 14244 the (co)polymers based on the monomers 1 -1 to 1 -18, J P2010040830 the compounds HA-1 to HA-20, HB-1 to HB-16, HC- 1 to HC-23 and the (co)polymers based on the monomers HD-1 to HD-12, JP2009021336, WO2010090077 the compounds 1 to 55, WO2010079678 the compounds H 1 to H42,
  • WO2010067746, WO2010044342 the compounds HS-1 to HS-101 and Poly-1 to Poly-4, JP20101 14180 the compounds PH-1 to PH-36, US2009284138 the compounds 1 to 1 1 1 and H 1 to H71 , WO2008072596 the compounds 1 to 45, JP2010021336 the compounds H-1 to H- 38, preferably H-1 , WO2010004877 the compounds H-1 to H-60, JP2009267255 the compounds 1 -1 to 1 -105, WO2009104488 the compounds 1 -1 to 1 -38, WO2009086028,
  • WO2010087222 the compounds H-1 to H-31 , WO2010095564 the compounds HOST-1 to HOST-61 , WO2007108362, WO2009003898, WO2009003919, WO2010040777,
  • the host materials mentioned above may be used in the OLED of the present invention alone or in combination with the compound of general formula (I) or (1 1 ) as host material.
  • the compound of general formula (I) or (1 1 ) is the host and the host materials mentioned above are the co-hosts.
  • Examples of the compounds which are suitable as phosphorescent host, alone or in combination with the compound of general formula (I) or (1 1 ) as host material include a carba- zole derivative, a triazole derivative, a oxazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phe- nylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, a styrylanthracene derivative, a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aromatic tertiary amine compound, a styrylamine compound, an aromatic methylidene compound, a porphyrin compound, an anthraquinodimethane derivative, an anthrone derivative, a diphenylquinone derivative,
  • the first host material mentioned in US20132341 19 which is preferably used as co-host together with at least one compound of general formula (I) or (1 1 ) in the light emitting layer of an OLED according to the present invention is represented by formula (A).
  • the lifetime of an OLED is increased by using as a first host material at least one compound of general formula (I) or (1 1 ) and as co-host the host material represented by formula (A) in the light emitting layer:
  • each of A 1A and A 2A independently represents an aryl group having 6 to 30 ring carbon atoms, which may be unsubstituted or substituted; or a heterocyclic group having 5 to 30 ring atoms, which may be unsubstituted or substituted;
  • a 3A represents a divalent aryl group having 6 to 30 ring carbon atoms, which may be unsubstituted or substituted; or a divalent heterocyclic group having 5 to 30 ring atoms, which may be unsubstituted or substituted;
  • mA represents an integer of 0 to 3; each of X 1A to X 8A and Y 1A to Y 8A independently represents N or CR a each of R a independently represents a hydrogen atom, an aryl group having 6 to 30 ring carbon atoms, which may be unsubstituted or substituted; a heterocyclic group having 5 to 30 ring at- oms, which may be unsubstituted or substituted; an alkyl group having 1 to 30 carbon atoms, which may be unsubstituted or substituted for example by E; a silyl group, which may be unsubstituted or substituted; a halogen atom, or a cyano group, provided that
  • At least one of A 1A and A 2A represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring at- oms;
  • At least one of X 1A to X 4A and Y 5A to Y 8A represents CR a , and at least one of R a in X 1A to X 4A and Y 5A to Y 8A represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms;
  • mA represents an integer of 1 to 3 and at least one of A 3 represents a cyano-substituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted divalent heterocyclic group having 5 to 30 ring atoms;
  • At least one of X 5A to X 8A and Y 1A to Y 4A represents CR a , and at least one of R a in X 5A to X 8A and Y 1A to Y 4A represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms; and
  • the cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and the cyano-substituted heterocyclic group having 5 to 30 ring atoms may be further substituted by a group other than the cyano group.
  • mA is preferably 0 to 2 and more preferably 0 or 1 .
  • mA is 0, one of X 5A to
  • X 8A and one of Y 1A to Y 4A are bonded to each other via a single bond.
  • the aromatic hydrocarbon group having 6 to 30 ring carbon atoms represented by A 1A A 2A and R a may be a non-condensed aromatic hydrocarbon group or a condensed aromatic hydrocarbon group. Specific examples thereof include phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, quaterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, spirofluorenyl group, 9,9-diphenylfluorenyl group, 9,9'- spirobi[9H-fluorene]-2-yl group, 9,9-dimethylfluorenyl group, benzo[c]phenanthrenyl group, ben- zo[a]triphenylenyl group, naphtho[1 ,2-c]phenanthrenyl group, naphtho[1 ,2-a]triphenyleny
  • Examples of the divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms represented by A 3A include divalent residues of the above aromatic hydrocarbon groups having 6 to 30 ring carbon atoms.
  • the heterocyclic group having 5 to 30 ring atoms represented by A 1A , A 2A and R a may be a non- condensed heterocyclic group or a condensed heterocyclic group.
  • Specific examples thereof include the residues of pyrrole ring, isoindole ring, benzofuran ring, isobenzofuran ring, diben- zothiophene ring, isoquinoline ring, quinoxaline ring, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, ox
  • Examples of the divalent heterocyclic group having 5 to 30 ring atoms represented by A 3A include divalent residues of the above heterocyclic group having 5 to 30 ring atoms.
  • alkyl group having 1 to 30 carbon atoms represented by R a examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n- decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n- pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1 -methylpentyl group, cyclopropyl group, cyclobuty
  • Examples of the silyl group which may be unsubstituted or substituted ; represented by R a in- elude trimethylsilyl group, triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t- butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylisopropylsi- lyl group, dimethylpropylsilyl group, dimethylbutylsilyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, diphenylter- tiarybutylsilyl group, and triphenylsilyl group, with trimethylsilyl group, triethylsilyl group, t- butyldimethylsilyl group, vinyldimethylsily
  • halogen atom represented by R a examples include fluorine, chlorine, bromine, and iodine, with fluorine being preferred.
  • R a is a hydrogen atom or an aryl group having 6 to 30 ring carbon atoms, which may be unsubstituted or substituted.
  • Examples of the optional substituent indicated by "substituted or unsubstituted” and “may be substituted” referred to above or hereinafter include a halogen atom (fluorine, chlorine, bromine, iodine), a cyano group, an alkyl group having 1 to 20, preferably 1 to 6 carbon atoms, a cycloal- kyl group having 3 to 20, preferably 5 to 12 carbon atoms, an alkoxyl group having 1 to 20, preferably 1 to 5 carbon atoms, a haloalkyl group having 1 to 20, preferably 1 to 5 carbon atoms, a haloalkoxyl group having 1 to 20, preferably 1 to 5 carbon atoms, an alkylsilyl group hav- ing 1 to 10, preferably 1 to 5 carbon atoms, an aromatic hydrocarbon group having 6 to 30, preferably 6 to 18 ring carbon atoms, an aryloxy group having 6 to 30, preferably 6 to 18 ring carbon atoms, an arylsily
  • Examples of the optional alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, and 1 - methylpentyl group.
  • Examples of the optional cycloalkyl group having 3 to 20 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, and adamantyl group.
  • Examples of the optional alkoxyl group having 1 to 20 carbon atoms include those having an alkyl portion selected from the alkyl groups mentioned above.
  • Examples of the optional haloalkyi group having 1 to 20 carbon atoms include the alkyl groups mentioned above wherein the hydrogen atoms thereof are partly or entirely substituted by halogen atoms.
  • Examples of the optional haloalkoxyl group having 1 to 20 carbon atoms include the alkoxyl group mentioned above wherein the hydrogen atoms thereof are partly or entirely substituted by halogen atoms.
  • Examples of the optional alkylsilyl group having 1 to 10 carbon atoms include trimethylsilyl group, triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylisopropylsilyl group, dime- thylpropylsilyl group, dimethylbutylsilyl group, dimethyltertiarybutylsilyl group, and diethyli- sopropylsilyl group.
  • Examples of the optional aryl group having 6 to 30 ring carbon atoms include those selected from the aryl groups mentioned above with respect to A 1A , A 2A and R a .
  • Examples of the optional aryloxy group having 6 to 30 ring carbon atoms include those having an aryl portion selected from the aromatic hydrocarbon groups mentioned above.
  • Examples of the optional arylsilyl group having 6 to 30 carbon atoms include phenyldimethylsilyl group, diphenylmethylsilyl group, diphenyltertiarybutylsilyl group, and triphenylsilyl group.
  • Examples of the optional aralkyl group having 7 to 30 carbon atoms include benzyl group, 2- phenylpropane-2-yl group, 1 -phenylethyl group, 2-phenylethyl group, 1 -phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, a-naphthylmethyl group, 1 -a-naphthylethyl group, 2-a-naphthylethyl group, 1 -a-naphthylisopropyl group, 2-a-naphthylisopropyl group, ⁇ - naphthylmethyl group, ⁇ - ⁇ -naphthylethyl group, 2- -naphthylethyl group, ⁇ - ⁇ -naphthylisopropyl group, 2- -naphthylisopropy
  • Examples of the optional heteroaryl group having 5 to 30 ring atoms include those selected from the heterocyclic groups mentioned above with respect to A 1A , A 2A and R a .
  • carbon number of a to b in the expression of "substituted or unsubstituted X group having carbon number of a to b" is the carbon number of the unsubstituted X group and does not include the carbon atom of the optional substituent.
  • the hydrogen atom referred to herein includes isotopes different from neutron numbers, i.e., light hydrogen (protium), heavy hydrogen (deuterium) and tritium.
  • the groups represented by formulae (a) and (b) are bonded to each other via -(A 3 ) m A- at one of X 5A to X 8A and one of Y 1A to Y 4A .
  • the bonding manner between formulae (a) and (b) are represented by X 6A -(A 3A ) mA -Y 3A , X 6A -(A 3A ) mA -Y 2A , or X 7A - (A 3A ) mA -Y 3A , namely the material for organic electroluminescence device is preferably represent- ed b formula (XXII), (XXIII), or (XXIV):
  • ⁇ 1 ⁇ to ⁇ 8 ⁇ , ⁇ 1 ⁇ to ⁇ 8 ⁇ , ⁇ 1 ⁇ to ⁇ 3 ⁇ , and mA are the same as X 1A to X 8A , Y 1A to Y 8A , A 1A to A 3A , mA in formula (A), and each of formulae (XXII), (XXIII), and (XXIV) satisfies at least one of the requirements (i) to (v) as specified in the definition of formula (A).
  • the host material represented by formula (A) satisfies at least one of the requirements (i) to (v), namely, the host material is a cyano group-introduced biscarbazole derivative having a group represented by formula (a) and a group represented by formula (b) which are linked to each other.
  • a 3A of formula (A) preferably represents a single bond, a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted divalent monocyclic heterocyclic group having 6 or less ring atoms.
  • Examples of the monocyclic hydrocarbon group having 6 or less ring carbon atoms represented by A 3A include phenylene group, cyclopentenylene group, cyclopentadienylene group, cyclo- hexylene group, and cyclopentylene group, with phenylene group being preferred.
  • Examples of the monocyclic heterocyclic group having 6 or less ring atoms represented by A 3A include pyrrolylene group, pyrazinylene group, pyridinylene group, furylene group, and thio- phenylene group.
  • mA is 0 and one of X 5A to X 8A and one of Y 1A to Y 4A are bonded to each other via a single bond; or
  • a 3A represents the substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring carbon atoms or the substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring atoms.
  • mA is 0 and one of X 5A to X 8A and one of Y 1A to Y 4A are bonded to each other via a single bond; or A 3A represents a substituted or unsubstituted phenylene group.
  • the host material of formula (A) satisfies preferably at least one of the requirements (i) and (ii);
  • At least one of A 1A and A 2A represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms;
  • At least one of X 1A to X 4A and Y 5A to Y 8A represents CR a
  • at least one of R a in X 1A to X 4A and Y 5A to Y 8A represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms.
  • the host material of formula (A) is preferably any one of the compounds
  • the host material of formula (A) satisfying the requirement (i) and/or (ii) has a structure wherein the cyano group-containing aromatic hydrocarbon group or the cyano group-containing hetero- cyclic group is introduced to the terminal end of the central skeleton comprising the groups represented by formulae (a) and (b).
  • At least one of A 1A and A 2A is preferably a cyano-substituted phenyl group, a cyano-substituted naphthyl group, a cyano- substituted phenanthryl group, a cyano-substituted dibenzofuranyl group, a cyano-substituted dibenzothiophenyl group, a cyano-substituted biphenyl group, a cyano-substituted terphenyl group, a cyano-substituted 9,9-diphenylfluorenyl group, a cyano-substituted 9,9'-spirobi[9H- fluorene]-2-yl group, a cyano-substituted 9,9'-dimethylfluorenyl group, or a cyano-substituted triphen
  • the host material of formula (A) wherein A 1A is substituted by a cyano group and A 2A is not substituted by a cyano group is preferred.
  • the first host material which does not satisfy the requirement (ii) is more preferred.
  • At least one of X 1A to X 4A and Y 5A to Y 8A is preferably CR a
  • one of R a in X 1A to X 4A and Y 5A to Y 8A is preferably a cyano-substituted phenyl group, a cyano-substituted naphthyl group, a cyano-substituted phenan- thryl group, a cyano-substituted dibenzofuranyl group, a cyano-substituted dibenzothiophenyl group, a cyano-substituted biphenyl group, a cyano-substituted terphenyl group, a cyano- substituted 9,9-diphenylfluorenyl group, a cyano-substituted 9,9'-spirobi[9H-
  • a 1A and A 2A are preferably different from each other, and more preferably, A 1A is substituted by a cyano group but A 2A is not substituted by a cyano group.
  • the host material of formula (A) is preferably structurally asymmetric.
  • the production method of the first host material is not particularly limited and it is produced according to a known method, for example, by a coupling reaction of a carbazole derivative and an aromatic halogenated compound in the presence of a copper catalyst described in Tetrahedron 40 (1984) 1435 to 1456 or a palladium catalyst described in Journal of American Chemical Society 123 (2001 ) 7727 to 7729.
  • the compounds according to general formulae (I) and (1 1 ) can also be used in combination with host materials that are called "second host materials" in US201302341 19, see in particular paragraphs 0146 to 0195 of US201302341 19.
  • these compounds according to paragraphs 0146 to 1095 of US201302341 19 can also be used as single host material in the electronic device according to the present invention, for example for red emitter material or green emitter material, preferably for red emitter material.
  • the use of compounds according to general formulae (I) and (1 1 ) according to the present invention in combination with host materials according to paragraphs 0146 to 0195 of US201302341 19 as host material for green light emitting materials is preferred.
  • Z 1 represents a ring structure fused to the side a and represented by formula (1 -1 ) or (1 -2), and Z 2 represents a ring structure fused to the side b and represented by formula (1-1 ) or (1 -2), provided that at least one of Z 1 and Z 2 is represented by formula (1 -1 );
  • M 1 represents a substituted or unsubstituted nitrogen-containing aromatic heteroring having 5 to 30 ring atoms
  • L 1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring atoms, or a group in which the preceding groups are directly linked to each other; and k represents 1 or 2.
  • a side c is fused to the side a or b of formula (1 ).
  • any one of sides d, e and f is fused to the side a or b of formula (1 ).
  • X 11 represents a sulfur atom, an oxygen atom, N— R 19 , or C(R 20 )(R 21 ); and each of R 11 to R 21 inde- pendently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms
  • the nitrogen-containing aromatic heteroring represented by M 1 of formula (1 ) includes an azine rings
  • nitrogen-containing aromatic heteroring examples include pyridine, pyrimidine, pyrazine, triazine, aziridine, azaindolizine, indolizine, imidazole, indole, isoindole, indazole, purine, pteri- dine, ⁇ -carboline, naphthyridine, quinoxaline, terpyridine, bipyridine, acridine, phenanthroline, phenazine, and imidazopyridine, with pyridine, pyrimidine, and triazine being particularly preferred.
  • the formula (1 ) is preferably represented by formula (2):
  • Z 1 represents a ring structure fused to the side a and represented by formula (1 -1 ) or (1 -2), and Z 2 represents a ring structure fused to the side b and represented by formula (1-1 ) or (1 -2), provided that at least one of Z 1 and Z 2 is represented by formula (1 -1 );
  • L 1 is as defined in formula (1 ); each of X 12 to X 14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1 , provided that at least one of X 12 to X 14 represents a nitrogen atom; each of Y 11 to Y 13 independently represents CH or a carbon atom bonded to R 31 or L 1 ; each of R 31 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubsti- tuted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alky
  • L 1 is as defined in formula (1 ); each of X 12 to X 14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1 , provided that at least one of X 12 to X 14 represents a nitrogen atom; each of Y 11 to Y 13 independently represents CH or a carbon atom bonded to R 31 or L 1 ; each of R 31 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted
  • L 1 is as defined in formula (1 ); each of X 12 to X 14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1 , provided that at least one of X 12 to X 14 represents a nitrogen atom; each of Y 11 to Y 13 independently represents CH or a carbon atom bonded to R 31 or L1 ; each of R 31 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted substituted or
  • M 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and each of p and s independently represents an integer of 0 to 4, and each of q and r independently represents an integer of 0 to 3.
  • R 51 to R 54 are as defined above with respect to formula (A).
  • Examples of the divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms and the divalent heterocyclic group having 5 to 30 ring atoms represented by L 1 to L 3 of formulae (1 ) to (4) includes divalent residues of the corresponding groups described above with respect to formula (A).
  • host materials according to US20140048784 in particular according to paragraphs 0098 to 0154 can be used in the electronic device according to the present invention, in particular, if red light emitting materials are used.
  • the host materials according to US20140048784 can be used as single host materials, which can is preferred, or can be used in combination with compounds (I), (II) or (III) according to the present invention as host material and co-host:
  • the host material according to US2014048784 is a biscarbazole derivative, having two carba- zole structures in a molecule thereof.
  • the biscarbazole derivative has, at a specific position, a substituted or unsubstituted fluoran- thenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted dibenzotriphenylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted benzo[b]fluoranthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothioph
  • each of A1 and A2 independently represents a substituted or unsubstituted aromatic hyd bon group having 6 to 30 ring carbon atoms
  • each of Y1 to Y16 independently represents C(R) or a nitrogen atom
  • each of R groups independently represents a hydrogen atom, a substituent, or a valence bonded to a carbazole skeleton
  • each of L1 and L2 independently represents a single bond, a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted, divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms, provided that; at least one of A1 , A2 and R represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenan- threnyl group, a substituted
  • At least one of Y1 to Y4 represents C(R), at least one of Y5 to Y8 rep- resents C(R), at least one of Y9 to Y12 represents C(R), and at least one of Y13 to Y16 represent C(R).
  • At least one of Y5 to Y8 represents C(R) and at least one of Y9 to Y12 represents C(R), wherein two R groups represent valences which are bonded to each other.
  • R groups in formulae (1 ) and (1 ') may be the same or different.
  • At least one of Y1 a to Y4a represents C(R)
  • at least one of Y5a to Y8a represents C(R)
  • at least one of Y9a Y12a represents C(R)
  • at least one of Y13a to Y16a repre- sents C(R).
  • At least one of Y5a to Y8a represents C(R) and at least one of Y9a to Y12a represents C(R), wherein two R groups represent valences which are bonded to each other.
  • the R groups in formula (1 a) may be the same or different.
  • At least one of Y1 ' to Y4' represents C(R')
  • at least one of Y5' to Y8' represents C(R')
  • at least one of Y9' to Y12' represents C(R')
  • at least one of Y13' to Y16' represents C(R').
  • At least one of Y5' to Y8' represents C(R') and at least one of Y9' to Y12' represents C(R'), wherein two R' groups represent valences which are bonded to each other.
  • R' groups in formula (10) may be the same or different.
  • each of A1 and A2 independently represents a substituted or unsubstituted aromatic hydrocar- bon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms; each of Y1 to Y16 independently represents C(R) or a nitrogen atom, and each of R groups independently represents a hydrogen atom, a substituent, or a valence bonded to a carbazole skeleton; and each of L1 and L2 independently represents a single bond, a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted, divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms, provided that: at least one of A1 , A2 and R represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group,
  • one of A1 a and A2a represents a group represented by formula (a) and the other represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzophenan- threnyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted ben- zo[b]fluoranthenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted binaphthyl group, a substituted or unsubstituted dibenzophenanthrenyl group, a substituted or unsubstituted naphthotriphenylenyl group, or a substituted or unsubstituted ben- zofluorenyl group; each of Y1 a to Y16a independently represents C(R) or a nitrogen atom, and each of R groups independently represents
  • each of Y21 and Y25 independently represents C(Ra) or a nitrogen atom, and each of
  • Ra groups independently represents a hydrogen atom or a substituent.
  • A1 a, A2a, Y1 a to Y16a, L1 a, L2a, and Ra in formulae (1 a) and (a) are the same as those of A1 , A2, Y1 to Y16, L1 , L2, and R in formula (1 ).
  • A1 a and A2a represents a group represented by formula (a) and the other represents a group including a large molecular weight fused ring, such as a triphenylenyl group and a chrysenyl group
  • the compound represented by formula (1 a) has an excessively large molecular weight, increasing the vapor deposition temperature and therefore likely to increase the amount of thermally decomposed components. Therefore, when one of A1 a and A2a represents a group represented by formula (a), the other preferably represents a substituted or unsubstituted fluoranthenyl group or a substituted or unsubstituted phenanthrenyl group.
  • one of A1 ' and A2' represents a substituted or unsubstituted naphthyl group or a substituted or unsubstituted fluorenyl group and the other represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; each of Y1 ' to Y16' independently represents C(R') or a nitrogen atom, and each of R' groups independently represents a hydrogen atom, a substituent, or a valence bonded to a carbazole skeleton; and each of L1 ' and L2' independently represents a single bond, a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted, divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms.
  • A1 ', A2', L1 ', L2', Y1 ' to Y16', and R' in formula (10) are the same as those of A1 , A2, L1 , L2, Y1 to Y16, and R in formula (1 ).
  • At least one of A1 , A2 and R preferably represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a sub- stituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted benzotri- phenylenyl group, a substituted or unsubstituted dibenzotriphenylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted benzo[b]fluoranthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofur
  • At least one of A1 and A2 represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted benzotri- phenylenyl group, a substituted or unsubstituted dibenzotriphenylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted benzo[b]fluoranthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophen
  • each of A1 and A2 in formulae (1 ) to (4) and (1 ') independently represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
  • -L1 -A1 and -L2-A2 in formulae (1 ) to (4) and (1 ') are preferably different from each other.
  • the substituted or unsubstituted phenyl group for any of A1 , A2 and R is preferably a phenyl group substituted by an aromatic hydrocarbon group having 10 to 30 ring carbon atoms and particularly preferably a naphthylphenyl group.
  • the biscarbazole derivative is particularly preferred as a host material to be used in combination with a green emitting dopant.
  • Y21 and/or Y25 preferably represents a nitrogen atom, and each of Y22 and Y24 more preferably represents C(Ra).
  • substituents represented by R and Ra include a fluorine atom; a cyano group; a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms; a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms; a linear, branched, or cyclic, divalent, unsaturated hydrocarbon group having 1 to 20 carbon atoms; a substituted or unsubstituted, linear, branched, or cyclic alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted, linear, branched, or cyclic haloalkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted, linear, branched, or cyclic haloalkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted, linear, branched, or cyclic haloalkoxy
  • the R groups on adjacent ring carbon atoms may be bonded to each other to form a ring structure together with the ring carbon atoms.
  • Examples of the linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a n-nonyl group, a n-decyl group, a n-undecyl group, a n-dodecyl group, a n- tridecyl group, a n-tetradecyl group, a n-pentadecyl group, a n-hexadecyl group, a n-heptadecyl group, a
  • Examples of the linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms include an ethylene group, a propylene group, and a butylene group.
  • 20 carbon atoms include a 1 ,3-butadiene-1 ,4-diyl group.
  • Examples of the linear, branched, or cyclic alkylsilyl group having 1 to 10 carbon atoms include a trimethylsilyl group, a triethylsilyl group, a tributylsilyl group, a dimethylethylsilyl group, a dime- thylisopropylsilyl group, a dimethylpropylsilyl group, a dimethylbutylsilyl group, a dimethyl-t- butylsilyl group, and a diethylisopropylsilyl group.
  • Examples of the arylsilyl group having 6 to 30 carbon atoms include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl-t-butylsilyl group, and a triphenylsilyl group.
  • halogen atom examples include a fluorine atom.
  • aromatic heterocyclic group having 2 to 30 ring carbon atoms examples include non- fused aromatic heterocyclic and fused aromatic heterocyclic groups, more specifically, a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indolyl group, an isoindolyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a carbazolyl group, a phe- nanthridinyl group, an acridinyl group, a phenanthrolinyl group, a thienyl group, and residues of a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring,
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms include non- fused aromatic hydrocarbon groups and fused aromatic hydrocarbon groups, more specifically, a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a fluoranthenyl group, a triphenylenyl group, a phenanthrenyl group, a 9,9- dimethylfluorenyl group, a benzo[c]phenanthrenyl group, a benzo[a]triphenylenyl group, a naph- tho[1 ,2-c]phenanthrenyl group, a naphtho[1 ,2-a]triphenylenyl group, a dibenzo[a,c]triphenylenyl group, and a benzo[b]fluoranthenyl group.
  • Examples of the divalent linking group represented by L1 and L2 in formulae (1 ) to (4) and (1 ') include a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted, divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms.
  • Examples of the divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms include groups obtained by making the examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms mentioned above into divalent groups.
  • divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms include groups obtained by making the examples of the aromatic heterocyclic group having 2 to 30 ring carbon atoms mentioned above into divalent groups.
  • Y1 to Y16 all preferably represent C(R).
  • the number of substituents represented by R in Y1 to Y8 or in Y9 to Y16 is preferably 0 to 2, more preferably 0 or 1 .
  • biscarbazole derivative represented by any one of formulae (1 ) to (4), (1 '), and (10) include the following compounds.
  • D represents a heavy hydrogen (deuterium).
  • the compounds according to general formulae (I) and (1 1 ) are preferably be used as host material in the light emitting layer of the electronic device, preferably in a OLED, according to the present invention.
  • the compounds according to general formulae (I) and (1 1 ) can be used (a) as single host materials or can be used (b) in combination with any compounds suitable as host materials as mentioned above.
  • Embodiment (a) is preferred; if a red light emitting material is present in the light emitting layer.
  • Embodiment (b) is preferred; if a green light emitting material is present in the light emitting layer.
  • Preferred host materials which may be used, if blue dopants are present in the light emitting layer, are mentioned in US 2012/1 12169.
  • Ar 11 and Ar 12 are independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group formed by combination of a monocyclic group and a fused ring group and Rioi to R108 are independently a group selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, a group formed by combination of a monocyclic group and a fused ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
  • the monocyclic group in the formula (5) means a group which is composed only of ring structures having no fused structure.
  • aromatic groups such as a phenyl group, biphenyl group, terphenyl group and quaterphenyl group
  • heterocyclic groups such as a pyridyl group, pyradyl group, pyrimidyl group, triadinyl group, furyl group and thienyl group, can be given preferably.
  • a phenyl group, biphenyl group or terphenyl group is preferable.
  • the fused ring group in the formula (5) means a group formed by fusion of 2 or more ring structures.
  • fused ring group having 8 to 50 (preferably 8 to 30, more preferably 8 to 20) ring atoms fused aromatic ring groups such as a naphthyl group, phenanthryl group, anthryl group, chrysenyl group, benzanthryl group, benzophenanthryl group, triphenylenyl group, benzochrysenyl group, indenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, ben- zofluorenyl group, dibenzofluorenyl group, fluoranthenyl group and benzofluoranthenyl group, and fused heterocyclic groups such as a benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, quinolyl group and phenanthrolinyl group, can be given preferably.
  • fused aromatic ring groups such
  • a naphthyl group, phenanthryl group, anthryl group, 9,9-dimethylfluorenyl group, fluoranthenyl group, benzanthryl group, dibenzothiophenyl group, dibenzofuranyl group or car- apelolyl group is preferable.
  • a monocyclic group, fused ring group, alkyl group, cycloalkyl group, silyl group, alkoxy group, cy- ano group and halogen atom (in particular, fluorine) can be given.
  • a monocyclic group and fused ring group are particularly preferable.
  • anthracene derivative represented by the formula (5) be any of the following anthracene derivatives (A), (B) and (C), which is selected depending on the constitution or demanded properties of an organic EL device to which it is applied.
  • This anthracene derivative is derivatives of the formula (5) wherein Ar 11 and Ar 12 are independently a substituted or unsubstituted fused ring group having 8 to 50 ring atoms.
  • This anthracene derivative can be classified into the case that Ar 11 and Ar 12 are the same substituted or unsubstituted fused ring group and the case that Ar 11 and Ar 12 are different substituted or unsubstituted fused ring groups.
  • the fused ring are the same as those described above.
  • a naphthyl group, phenanthryl group, benzanthryl group, 9,9-dimethylfluorenyl group and dibenzofuranyl group are preferable.
  • This anthracene derivative is derivatives of the formula (5) wherein one of Ar 11 and Ar 12 is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, and the other is a sub- stituted or unsubstituted fused ring group having 8 to 50 ring atoms.
  • Ar 12 is a naphthyl group, phenanthryl group, benzanthryl group, 9,9-dimethylfluorenyl group or dibenzofuranyl group
  • Ar 11 is a phenyl group substituted by a monocyclic group or fused ring group.

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Abstract

La présente invention concerne des composés de formule générale (11), un matériau pour un dispositif organique électroluminescent comprenant au moins un de ces composés, un dispositif électroluminescent organique comprenant au moins un de ces composés et l'utilisation d'un composé de formule générale (11) dans un dispositif électroluminescent organique comme matériau hôte ou matériau transporteur d'électrons. (Formule 11)
PCT/IB2016/057876 2015-12-21 2016-12-21 Composés hétérocycliques azotés et dispositifs électroluminescents organiques contenant ceux-ci WO2017109722A1 (fr)

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EP3339293A4 (fr) * 2015-09-24 2018-07-04 LG Chem, Ltd. Composé et dispositif optoélectronique organique le comprenant
EP3498700A1 (fr) 2017-12-15 2019-06-19 Idemitsu Kosan Co., Ltd. Dérivé hétérocyclique contenant de l'azote, matériau pour élément électroluminescent organique l'utilisant et élément électroluminescent organique et dispositif électronique l'utilisant
US10562889B2 (en) * 2016-04-01 2020-02-18 Impact Therapeutics, Inc. Process for the preparation of 1-(arylmethyl)quinazoline-2,4(1H,3H)-diones
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EP3680242A1 (fr) 2019-01-10 2020-07-15 Idemitsu Kosan Co., Ltd. Dispositif électroluminescent organique et composés à utiliser en son sein
US11111244B2 (en) 2018-10-08 2021-09-07 Luminescence Technology Corp. Organic compound and organic electroluminescence device using the same
WO2022260096A1 (fr) 2021-06-11 2022-12-15 東ソー株式会社 Matériau d'élément de conversion photoélectrique pour élément d'imagerie et élément de conversion photoélectrique pour élément d'imagerie

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KR20180065353A (ko) * 2016-12-07 2018-06-18 롬엔드하스전자재료코리아유한회사 유기 전계 발광 재료 및 이를 포함하는 유기 전계 발광 소자
EP3418285B1 (fr) * 2017-06-20 2020-05-06 Idemitsu Kosan Co., Ltd. Composition comprenant un complexe d'ir substitué et une phenylquinazoline pontée avec un hétéroatome
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KR102353985B1 (ko) * 2019-01-09 2022-01-21 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20200099651A (ko) 2019-02-14 2020-08-25 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함한 발광 장치
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